Trials of a Responsible Hedonist

December 18, 2007 1:11 PM

Peripatetic, endearingly-awkward geek seeks amazing advice for casual sex shenanigans.

I recently completed my first serious relationship, a year-long cohabitation. It ended, in large part because I'm just not ready to settle down - I'm young (24), and I've still got an itch to scratch (although this former girlfriend is still one of my dearest friends in the world). I travel from job to job, from oceanography in the Pacific Ocean to (as of March) a stint in Japan. This wanderlust is the bee's knees, but does not provide the foundation for serious romantic roots.

So I come to you, hive mind, to bestow me with your collective wisdom on casual sex mojo.

I am not a total novice in this arena. Of the dozen+ women I've been lucky enough to somehow bed, most have been one-nighters with women 5-10 years older than I, and whose ranks have included PhDs, a fetish model or two, and a disproportionate number of redheads. This sounds grand, until you realize that most of this action has been courtesy of: sex parties, and Craigslist.

I know - I know, OK? Not a real source of pride. But what few sex parties I've attended have always been fascinating and hilarious, even though nine times out of ten I ended up reading books (I come prepared) or dancing. My own Craigslist postings - posted here and here for your edification - prompt fan mail, but no real results (the internet is made of flakes).

Yet I have, in fact, approached (hundreds?) of women on subways and city streets (mostly in NYC) to tell them them they're gorgeous, and ask them out on the spot - most are taken, it's never proceeded past a coffee even if they're single, but 99% were grinning a mile-wide even if they said "No." (Perhaps I was too young? At its height, I was 20 or 21). Nevertheless, the abysmal success rate did do a number on my self-confidence. Fact is, I would very much like to meet a lovely lady or two in the flesh, while out on the town, and woo her by virtue of my own merits.

I just have no idea how. Help a man out.

Pros: I am, apparently, quite attractive - I regularly sport pinstripes and a fedora, and I'm informed that pictures of me prompt girly coos (which confuses no one more than me). I have a natural accent - I am often thought to be either British or Eastern European (having lived in both places), despite being born and raised in the States. I read everything I get my hands on, and have wacky tales of adventure to amuse and intrigue. I also tear up the dance floor at clubs.

Cons: I don't drink or frequent bars, depriving me of valuable social lubricant. I am effectively blind to female social cues and come-ons (friends and family have to tell me what I've missed), and I couldn't muster decent innuendo if I tried. And I worry that, at first glance, I'm really quite creepy: I can't manage small talk for the life of me, don't match any standard of hip (no drugs, infinitely obscure interests), and regularly provoke comments about my 'intensity.' I also enjoy treating people like human beings - which, I'm told, does not raucous casual sex make.

Remember: I'm looking for advice, not lectures. For your information, I have never, ever cheated on a girl, and I have never, ever had unprotected sex - despite which, I get tested every six months out of civic responsibility. I am, in fact, a big fan of falling down emotional rabbit holes with brilliant, badass women - but that's simply not what my life allows for right now.

I believe that you should leave your lovers better than you found them. Because this isn't even about sex, really - it's about having fabulous adventures with wonderful people. Just in bed.

What works? What doesn't? What might? I'm at [e-mail]. Thank you in advance. You're all beautiful.

posted by anonymous to human relations (113 comments total)

Just one observation: your Craigslist ads make you sound really pretentious. Serious and full of yourself. You need to figure out how to come off as more relatable.
posted by cmgonzalez at 1:22 PM on December 18, 2007 [6 favorites]

You seem to be incredibly fascinated with yourself, and with your carefully crafted affectations and faux-anachronistic diction.

Try turning the spotlight away from yourself, and shining it on other people. Think about their likes and dislikes. What makes them interesting, and not so interesting. Give it a shot. Hey. Other people are fascinating! You'll see.

In short, stop being self-obsessed.
posted by Gordion Knott at 1:26 PM on December 18, 2007 [12 favorites]

You're trying too hard. Way, way too hard.
posted by hollisimo at 1:28 PM on December 18, 2007 [22 favorites]

Well this bookworm LOVED your ads and had I been seeking something of that nature, you'd have been my first response.
posted by otherwordlyglow at 1:29 PM on December 18, 2007

For one, I think your CL ads don't get real responses because they are overwrought and reek of someone trying very, very hard to be ironic, iconoclastic, funny, witty, knowing, well-read, well-cultured and cute all at once, while winking at the reader, chucking her on the chin and elbowing her lightly in the ribs. I would take it down a notch or two and see what results you get. Be a real person. Sure, make a couple references to stuff you like so they know where you're coming from, but glib is a turnoff. I don't think the "internet is full of flakes" argument bears out anymore. People meet and date successfully on the internet all the time these days. I posted a short, funny, smart CL ad and met my gf of 2+ years. I know you're not in the market for a long term relationship, but my point is that it's definitely possible to meet people online.
posted by sneakin at 1:30 PM on December 18, 2007 [5 favorites]

Fact is, I would very much like to meet a lovely lady or two in the flesh, while out on the town, and woo her by virtue of my own merits.

Honestly, this doesn't happen nearly as much as you may believe. That you have been generally unsuccessful may be as much a fact of the time as it is your "technique."
posted by wemayfreeze at 1:31 PM on December 18, 2007

Also, if you're asking "hundreds" of women and "most" are taken, it's probably more about you than their relationship status.
posted by sneakin at 1:33 PM on December 18, 2007 [1 favorite]

even if we don't consider the craiglist personals (frankly, the author sounds like an asshole, you should probably rewrite them to sound less like one), you're someone who after attending orgies & hitting on hundred of innocent random women in the subway has only slept with 12 (including, one assumes, the high school years and your ex live-in girlfriend); the results of your trying -- way too hard -- are very disappointing. you have two choices: try harder or not as hard.

my theory: try less hard, much less, to impress. listen more, you sound way more fascinated by yourself than by your prospective partner, and this is a big no-no, even if you're just looking for sex and not for a stable relationship. and please lose the fucking fedora, you're 24, you look like a tool.

if all else fails and you're still as horny as you sound like you are now, consider, to borrow your craiglist affectations, purchasing female companionship.
posted by matteo at 1:34 PM on December 18, 2007 [20 favorites]

Wow. Your email address, craigslist ad & general narcissism are pretty unappealing. try being interested in other people and speaking like a normal human being and you might have more luck. chicks dig guys who are honest with them AND honest with themselves. And right now, you're not that guy.
posted by luriete at 1:34 PM on December 18, 2007 [4 favorites]

Don't get me wrong, but if you're going to act all smarty-farty, don't have a grammatical error in the first sentence.

Also, brevity is the soul of wit. You can be smart without being frilly.

Also also, try OKCupid instead of Craigslist. It's less sleazy and there are pictures!
posted by Metroid Baby at 1:35 PM on December 18, 2007 [3 favorites]

So basically, you had eight paragraphs of "I am so great!" with what sounds like a bit of fake self-deprecation sprinkled in and one paragraph of actual question up there.

If these are the proportions involved when you talk to people, many of them aren't going to want to talk to you, much less have "fabulous adventures in bed" with you. You need to find a way to take yourself a notch. Maybe try Thai boxing for a while?
posted by ignignokt at 1:39 PM on December 18, 2007 [3 favorites]

I have a natural accent - I am often thought to be either British or Eastern European (having lived in both places), despite being born and raised in the States.

Some day you will look back on that and cringe. I hope.

Frankly, anonymous guy, I feel like you're the end product of way too much cheesy internet porn.

There's a dense mythology of men telling other men that there are lots and lots of girls who, when approached correctly, will want to have casual sex with them. Right?

And yet, I'm a girl. I know a ton of girls. I have, over the years, known maybe a handful of girls who claimed to be interested in casual sex, and perhaps one of them was not-crazy. Of my friends who have had drunken one-night stands, maybe three had an experience they didn't regret. And I don't have particularly conservative friends.

So where are all these girls who are dying to have no-strings sex with men? What if - I know, it sounds crazy, but stick with me for a minute here - what if this is a giant lie? What if there isn't actually a cohort of wild young bisexual coeds desperate to service strangers? What if this is a porn fantasy trope in much the same way that the hunky, commitment-hungry millionaire widowers who populate women's romance novels are also a fantasy trope?

If you put this in market terms, female sex trades at a much higher price than male sex. It trades at a so much higher price that women are routinely able to get men to pay to have sex with them. Sure, there are a few women (but I would really argue that you're wildly overestimating the number!) who are genuinely, healthily interested in casual sex, but first, their numbers are going to be tiny compared to the number of men interested in same, and since they are in essence a very rare sexual commodity, they can pretty much pick and choose. Right?

So what is your value-added? What are you bringing to the dance that should make the very few women interested in totally casual, no-relationship sex choose you?

I just don't think your fedora and fake accent are the draw you think they are. Maybe in person you're as geekily adorable as you seem to think, but maybe you're just in a no-win situation, where you're advertising something very few people are buying.
posted by thehmsbeagle at 1:39 PM on December 18, 2007 [122 favorites]

Seconding the ditching of the fedora.
posted by zsazsa at 1:40 PM on December 18, 2007 [2 favorites]

wow. you are trying way too hard. your ad makes you seem really judgmental--i imagine most women don't answer because they don't feel like they'd make the cut. you are really just showing off your vocabulary and your knowledge of pop culture using the medium of a personal ad.

i would pare it down significantly. also, walking up to a woman on the street is creepy (all it tells me is that you think i'm hot, which may be true, but not why i want to be singled out). stick to parties and other venues where conversation can emerge more naturally.

also, hooray, you've slept with 12 people by age 24. i know people who haven't slept with that many people by age 64. unless you hang out at bars or sex clubs, or you're never going to meet enough random women to have as much sex as you want. you'd do better cultivating a few f*ckbuddies than trying to arrange a random hookup every time you get a woody.
posted by thinkingwoman at 1:40 PM on December 18, 2007 [1 favorite]

You admit that you're "effectively blind" to female social cues.

It shows.

You need to open your eyes, tear yourself away from your inner monologue (no matter how fascinated you are by it), and start paying attention to other people. To girls. Pay attention to who they are, what they like, their quirks, their individual things that make them people. Stop spewing all this pretentious verbiage. Write the shortest CL posting you can stand, and then edit half of it out. And when you talk to someone, don't impose. It's clear that you find yourself fascinating, but you seem more taken by the idea of yourself then your actual observations and experiences. Kick yourself in the pants, get over it, and start experiencing the world like a person rather than the dapper literary chap you so dearly want to be.
posted by bassjump at 1:40 PM on December 18, 2007 [7 favorites]

Yeah, and there are two g's in "Juggs".
posted by BitterOldPunk at 1:41 PM on December 18, 2007 [10 favorites]

Yet I have, in fact, approached (hundreds?) of women on subways and city streets (mostly in NYC) to tell them them they're gorgeous, and ask them out on the spot - most are taken, it's never proceeded past a coffee even if they're single, but 99% were grinning a mile-wide even if they said "No."

Holy crap! You're the guy who harasses women on the street? I always wondered who that guy was! And your post, so arrogant and pretentious, well it is exactly the kind of writing I'd expect from someone who had the audacity to beg sex from strange women.

In short, don't do that. Those grins? Was it an actual grin, or that painful rictus women adopt when they're trying to exit a situation with a strange guy as fast as possible but are too scared to be violent towards him? Of course most of them are taken. Of course that's what they tell you. The vast majority of women will never respond positively to the solicitations of strange men, no matter who that man is. Men who come up and beg for sex or dates are generally creepy and/or offensive.

Anyway, your post and your Craigslist ads makes you sound pretty full of yourself. You've got some pseudo-modest self-affectation going on that is tremendously irritating ("I don't mean to brag, but I am incredibly awesome in every way"), and if you act anything like the way you write women can smell you trying too hard from about a mile away.

Relax. Quit obsessing over the hot women you've had sex with, the fedoras you wear, the women who are flattered by your attentions as if these are proof you deserve a mate. You don't. Nobody does. No matter how wonderful and amazing someone is, the only love (romantic or physical or otherwise) they'll get is the love they've displayed they're willing to give, and if you so much of your time is spent on yourself no person is going to think you're capable of loving anyone else. Join a club or something. Show interest in the actual activity instead of picking up women. Women respond to a man who acts like a human being instead of a cartoon wolf.
posted by schroedinger at 1:42 PM on December 18, 2007 [45 favorites]

It sounds to me like fast seduction/pickup artistry/neurolinguistic programming kinda stuff would be right up your alley.
posted by box at 1:44 PM on December 18, 2007

Seconding the okcupid and being less sleazy recommendations. San Diego craigslist is not your target audience. If you're looking for nerdy girls, go where the nerdy girls are, and explain your non-relationship-seeking status in a humble and appropriate manner so you don't come off as quite such a perv. No matter how horny the librarian, she doesn't want to sleep with someone who's trying to give the impression that they have lots of unsafe, casual sex. You're looking for *smart* girls, right?
posted by booknerd at 1:44 PM on December 18, 2007 [1 favorite]

An intense guy can accomplish a lot with eye contact. Scan the room, and if you notice a girl looking at you, hold her gaze and smile slightly until she looks away. Tilt your head and mouth something. If she's close enough to hear, whisper. Make her lean forward, and draw her into you.

IMO, many women either like to be diligently and persistently pursued, or not at all. (Note: it is no compliment to a woman to be pursued only to find out that the man is simply pursuing for sex.) Obviously diligence and persistence has not worked for you, so lean back and be the prey, and let the woman be the unwitting predator. I think that in this way, you have a greater chance of drawing out women that are interested in you for just sex, because those are more likely to be assertive types.
posted by desjardins at 1:45 PM on December 18, 2007

i agree completely with sneakin's description of how you come across in your writing. and that, in conjunction with the fact that you "regularly sport pinstripes and a fedora" (regardless of your age), have an "accent" as well as an insincere sounding self-effacing modesty is—while maybe interesting to another for about 15 minutes, just really reeks of a sort of smugness with your persona that is actually really boring and unattractive. you don't sound like a real or down-to-earth person. all of those things about yourself that you write about may not in fact be affectations but to other people you just might come across as really fake. it's not attractive to most people. that may be part of your difficulty in finding women because someone who is really attracted to that kind of persona is few and far between.

also, you sound like you are looking for a casual relationship but your post as well as your craigslist ads make it sound like you are looking for more than that. i ended up at the end of your post confused as to what you are really looking for.
posted by violetk at 1:47 PM on December 18, 2007 [1 favorite]

I'm so very much the last person on Earth who should be giving geek mating advice. See my latest question.

But looking at your Craigslist ads, I think the wit you're using is like a fine spice. Sprinkle it over a fine meal and you've just improved the flavor sevenfold. Unscrew the cap and dump the bottle's contents on the meal and you've just created an inedible mess. I mean that both as the compliment and chiding it is: you've got a talent for wit, but you're overusing it heavily, at least in those ads.

A few observations:

Cold approaches are very rarely successful, especially in non-social places like subways and city streets. If you want to do cold approaches, you'd probably have better luck in social locales where people come to congregate, such as coffeehouses, bars, and the places people are mentioning in my question. If you choose not to go to bars, then choose other places where people congregate. (I really don't usually drink that much either, but you can always order soda, juice, water, etc. Who is going to know the difference between a Diet Coke and a Coke 'n' rum, or an OJ and a screwdriver?)

As for female social cues and come-ons, it's definitely not my native language either; I once described myself to a friend as sexually autistic. I've found this to be of use, as well as some otherwise highly misogynistic writings by Michael Pilinski. Also, look for flirting classes in your area. For example, there's a woman-owned sex shop (difference, in case you're curious, seems to be: unashamed, non-seedy, clean, well-lit, uncreepily friendly staff) in the north Chicago area which has a lot of various "sex classes," including a class they call "Flirting for Nerds," etc. Look for something similar in your area.

Also, keep in mind that you are the universe you make, i.e., self-fulfilling prophecies. There's a lot of opinion stated as fact in your original post.

I'll be curious to read others' comments. I've got a few variants of various problems you mention above.
posted by WCityMike at 1:47 PM on December 18, 2007 [3 favorites]

nthing what everyone else has said -- you sound fascinated with yourself. Tone it down a bit, listen a lot more than you talk and rub one out more frequently.

This:

regularly provoke comments about my 'intensity'

Does not surprise me in the least.
posted by Pantengliopoli at 1:47 PM on December 18, 2007

I'm with Gordian Knot and sneakin. All the way.

Yet I have, in fact, approached (hundreds?) of women on subways and city streets (mostly in NYC) to tell them them they're gorgeous, and ask them out on the spot - most are taken, it's never proceeded past a coffee even if they're single, but 99% were grinning a mile-wide even if they said "No."

Are you really doing this? Dude. Of course they're saying no. You're acting foolish.

And it's a little grating that you seem to believe all these women who turned you down, were obviously kind of into you, or why else would they be grinning at you? Well, it's because they're afraid of hurting your feelings by rejecting you without adding friendliness to the matter. And at least some of those "taken" women invented boyfriends on the spot. God knows I've done that, when approached that way.

Advice: Tone down the annoying, play-acting pretentiousness. You're coming off as self-absorbed and obnoxious, but also completely clueless.
posted by Coatlicue at 1:48 PM on December 18, 2007

I am, apparently, quite attractive - I regularly sport pinstripes and a fedora

Yes, I hear the Nathan Detroit look is getting all the chicks this year.

To be more responsive to the question, I don't think showy affectation is a strong lead-in to casual sex.
posted by pardonyou? at 1:49 PM on December 18, 2007 [2 favorites]

Wow. Ok. Here comes some honesty: Your ads will never get you laid. Sorry. Maybe start off with something seriously less, well, ridiculous. "Male seeks smart, nerdy girl for romp in the hay," will do you WAY better. While they were funny (I chuckled out loud many times while reading them), I can't imagine anybody taking them seriously.

Now, when approaching women...well, you seem to have the confidence--just turn down the a. arrogance, and b. neediness. You sound arrogant in your ads and needy in person. Don't tell a women right away she's gorgeous. Don't flatter her at all right away. Just talk to her. That's it.

I've heard really good things about the book The Game. You might want to give it a read.

And if you want to meet people at parties/clubs, don't bring books. Nothing makes you seem like you don't want to meet anybody more. Watch people, make conversation. Hell, if you must have something written to look at, at least be doing a crossword. Just make sure you use it as a tool to meet somebody...("Hey, what's a five-letter word for...?")
posted by General Malaise at 1:50 PM on December 18, 2007

Your email indicates you are looking for a lot of NSA sex. Your track record isn't really bad at all if you're doing that--rejection is going to be the name of the game for most times, and you just volume deal to get a chance at what you want.

But cmgozalez has it, you seem not so relaxed. You are eager to show your credentials as if that helps with women. It doesn't. My experience is that people want to know you like them and why. Strangely enough, they really don't care about you.

Usually we see who we are with as a indicator of some sort of alleged "self-worth" that we have. If we believe this, it is natural to expect that enumerating one's "best features" is going to help us with the opposite sex.

I find it is just the opposite. List what you want, without doing it in such a way to make it sound like you are demanding. People will then think "hey, I'm beautiful, smart and funny" this guy will love me. Make it about them and not about you.

Try this: Intimate Connections
posted by Ironmouth at 1:52 PM on December 18, 2007 [1 favorite]

Dear lord, I love the hmsbeagle's and schroedinger's answers forever.
posted by Coatlicue at 1:53 PM on December 18, 2007 [1 favorite]

Oh, and take everybody else's advice at least from here up too.


Especially ditching the fedora. Or the pinstripes. Or both. At least one. The picture I have in my head is a little ridiculous.
posted by General Malaise at 1:56 PM on December 18, 2007 [1 favorite]

Maybe in person you're as geekily adorable as you seem to think, but maybe you're just in a no-win situation, where you're advertising something very few people are buying.

I would agree with thehmsbeagle. I don't know very many women who actively go out looking for casual, no-strings sex. All the girls I know who have a lot of casual sex are searching for their one true love (or at least pretending to).
posted by ThePinkSuperhero at 1:56 PM on December 18, 2007 [2 favorites]

OK, first of all, there are *plenty* of girls out there who *are* interested in casual sex. Many of them you wouldn't want a relationship with, but hey, who cares? You are definitely coming across a little bit "try-hard", but the important thing is that you have had the balls to approach these women. That is a major advantage you have over many people. The issue now is how to succeed. People don't like the fact, but there is a technique to being successful - google some of the pick-up artist stuff (and previously on MeFi). In particular read the blogs and decide who fits your style then attend some sort of training session. It's no different to any other skill. One guy I know who specialises in training to attract "same night lays" is Captain Jack from the Mystery Method crew. There is a LOT out there on this stuff!

Good luck, and if you can make the fedora work for you, stick with it...
posted by csg77 at 1:58 PM on December 18, 2007

Also also also, upon a second read-through, this phrase jumped out and kicked me in the eye:

I also enjoy treating people like human beings - which, I'm told, does not raucous casual sex make.

Oh, please. Do you for reals believe this or are you just affecting sarcasm? Maybe respect isn't essential for casual drunken fratboy meat-slapping-meat sex, but for actual good sex, respect is the bread and lube, even if it's someone you hook up with only once a year or once-ever. Casual sex is for good friends! (And good friends are for casual sex.)
posted by Metroid Baby at 1:59 PM on December 18, 2007 [8 favorites]

By the way: answers thus far are both OUCH! and useful to you, if you can look past the criticism.

AskMefites are usually not afraid of brutal honesty especially when the author is anonymous. I could see you reading this and being like, "Well, !@#$%^ them!!!!". But keep in mind you approached this forum asking for advice, not necessarily affirmation, as to your sexual and emotional approach towards women — and thus far it's a rather collective judgment that the way in you're approaching women is rather at odds with reality-based flirtation.

No one here, I think, means their advice maliciously. Even the more harshly worded comments are, I think, meant in a way akin to the "slap in the face" panic-stopping technique that you see in movies; the harshness is meant, I presume, as a means of jolting you out of your current way of viewing the "dating game."

Keep in mind that if you need to get a response back to the thread to anything, you can do so by e-mailing one of the mods (usually Jessamyn), and they'll post it.
posted by WCityMike at 1:59 PM on December 18, 2007 [1 favorite]

I'm both surprised and not surprised by the pile-on here. So, anon, I just want to say that when I was 23 or 25 I would have found your ad endearing and attractive.

And I like fedoras on men of all ages.

BUT. You are, alas, trying too hard. You sound like a fine young gentlemen who is a tad too sold on his own fineness and gentlemanliness (as it were). Take a hard advice here and discard a lot of the frippery and affectation you're working. Ease up on the whimsical, flowery prose. Not all ads need to be lean, muscular, two-sentence come-ons, but yours is ... well, there's too much there there.

Listen to me now: You are obviously smart and cool and interesting. But by TRUMPETING that AS QUIRKILY and LOUDLY as possible, you're going to repel the kind of smart, cool women you're looking for. Your essence will still come though clearly in a conversation in which you engage a woman about her interests and thoughts. So go have conversations with women about them, and just be yourself (not your idea of yourself) during them.
posted by minervous at 2:00 PM on December 18, 2007

Its a lot easier to "sound smart" when you arent trying so hard to sound smart. I am all for the occasional big word thrown in to edify my prose, but I realize that if I am using several of them a sentence I come across as a grandiose dickwad, and that is in academic papers, let alone a personal ad. So I am going to give you two pieces of advice here, first if you are going to keep on using craigslist, tone it down a little bit, and put in a picture, it doesnt need to be of you, its just to get more eyeballs on your ad. Second, dont try so hard, dating really isnt difficult if you pay attention to the girl and learn from your mistakes, be persistent but more importantly pay attention to the girl and pretty soon you will figure out what she wants to hear, and how she wants you to present yourself. You are obviously semi-intelligent, and honestly girls arent that difficult to figure out. Also dont expect sex on the first date, it takes a few, but if they make you wait too long and you arent interested in a real relationship with her then cut your losses and move on.
posted by BobbyDigital at 2:01 PM on December 18, 2007 [2 favorites]

You need to go to clubs!

This will help you in two ways. One, your affectation might make you seem like a "fun party guy" rather than how you are coming off now. Two, you will meet drunk women who are looking for guys.

And remember, when not in a club, less is more. You seemed to have got your signals crossed on that somehow.
posted by milarepa at 2:02 PM on December 18, 2007

To me, you're coming across as that guy, don't be that guy.

That said, when I had trouble meeting people I figured it was time to start doing something differently. Reading your post and craigslist posts, you come across as unable to evaluate yourself from a realistic view point.

Do you have a female friend that you haven't dated? If so, maybe ask her what she thinks you're doing wrong.

From my perspective, much of what you're doing seems to be the type of things people in their early twenties did. Ie. Purposefully dressing or talking different, worrying about frat boys, and dwelling on a long string of things that really don't matter.

Finally, it's better to have some mystery than to try to lay out how awesome you are beforehand. With the writing in your craigslist ad, it's almost impossible for you to live up to the grand image you present of yourself, so anyone is bound to be a bit disappointed if they believe the hype.
posted by drezdn at 2:04 PM on December 18, 2007 [2 favorites]

I am effectively blind to female social cues and come-ons (friends and family have to tell me what I've missed), and I couldn't muster decent innuendo if I tried. And I worry that, at first glance, I'm really quite creepy: I can't manage small talk for the life of me, don't match any standard of hip (no drugs, infinitely obscure interests), and regularly provoke comments about my 'intensity.'

(1) blind to social cues (2) can't do small talk (3) obscure interests (4) intense (5) self-absorbed. Did you know these all prominent features of Asperger's Syndrome? You might want to look into this as a cause of some of the issues you mention. Here's an article and quiz that can rule it in or out for you : http://www.wired.com/wired/archive/9.12/aqtest.html
posted by nancoix at 2:04 PM on December 18, 2007 [1 favorite]

Pinstripes? Fedora? Life of the party on the dance floor? Sex parties? Creeping out women in public?

Aside from the fake accent, it sounds like you're The Joker. And who knows? With Heath Ledger in the upcoming role, The Joker might have that, too.

Seriously, your whole style is wrong, from your clothes to your mannerisms to your approach to your writing style. Stop trying so hard to be a caricature of what you imagine to be a cultivated, intellectual man of mystery.

Or, alternatively, cheers on having crafted two humorous fake craigslist ads and one thought-provoking hoax of an AskMe thread.
posted by The World Famous at 2:07 PM on December 18, 2007 [19 favorites]

Remember: I'm looking for advice, not lectures

a-HEM.

Wear what you like, have whatever affectations you can sustain (everyone does, whether it's a corny gothic accent or brand loyalty to Sephora) and carry your head high. Confidence is, indeed, attractive, but people (around here, obviously, but elsewhere too) don't curry to reading all about it. So, do cultivate the ability to understate and self-deprecate. Unintended rhyming, sorry.

You need wingmen or gal-pals, I think. If a woman finds you appealing, but you're all on your own, it can be intimidating for her to be receptive. Triangulated social reactions are great. If she gets good corollary info about you by meeting your friends, or from seeing the reaction to you her friends have, that's great. So, go make friends or join clubs. LARPing? Renfaires? S&M? I mean there really are lots of social enclaves where costumey folks like you can pick ladies off like flies if you're as dope as you say. I should know.
posted by Ambrosia Voyeur at 2:08 PM on December 18, 2007 [1 favorite]

You know, when I was 18, I probably would have found you to be awesome. In fact, a guy similar to you - I would have thought it was the same guy, actually, except that he is probably 30 now and I hope to god he is not like this anymore - completely swept me off my feet when I was 19-20. He thought he was fantastic. He thought he was a good dancer. He thought he was really clever and funny. He told everyone "You're beautiful, baby" when people bought him drinks (it wasn't just women who were initially drawn to him). And he wore a fedora. (No pinstripes, though).

It took a lot of alcohol and one of my best male friends about six months' time to convince me that this guy was pretentious, was totally full of himself to the exclusion of everyone else around him and that he wasn't worth my time. Looking back from 27, I have no idea what I was thinking. He sounded dashing, attractive and smart but he was really none of those things. It was all an act. And he could never relax and Be Himself because I don't think he really knew who he was.

I don't know if your posturing for us all here is an act, but it certainly comes off as one. Take off the fedora, put on some jeans, stop with your ridiculous accent and just relax. Stop being so intense. Your ads on Craigslist are just... well, frankly, the word that came to mind was "git." You're so conscious of being clever and hip that it's painful. Why not just say, "Hey, I'm a geek seeking similar"? Why do you have to throw in so many pop culture references and words that make it look like you flipped through a thesaurus, searching for synonyms for "cool" or "obscure"? Look, I don't like fratboys either, but if you and one were to shake hands, you might cause an explosion? Lame.

And for goodness sake, stop approaching women in the subway or on the street. That screams "creep" to me like nothing else. I loathe being approached on the street and I know a lot of other women do, too.
posted by sutel at 2:08 PM on December 18, 2007 [5 favorites]

Oh my god, nthing the "trying too hard" thing. I love smarty-pants bibliophiles as much as the next girl, but you're going to 11, dude. To me, you're sending one of three messages: 1) "I'm 'on' ALL THE TIME, and you will have to keep up constantly, lest you be judged by my withering standards"; 2) "I'm shooting my wad -- this overcrafted schtick is all I got"; or 3) "I am desperately insecure and afraid of being seen as even remotely 'average.'" (Hint: none inspires much interest or desire.)

Based on having known more than one guy like this, I further suspect that, on dates, you either 1) talk incessantly about yourself, or 2) grill your date to see if she's got the goods to live up to your fantasy. Again: been there, done that, couldn't WAIT to for the date to be over.

Tone it down. I'm not saying that you have to adopt another schtick (in this case, the schtick of being "mysterious"), but I am saying that you need to take a breath. Don't lay it all out. Cut way back on the hyperbole. Don't pretend to be a character in the movie of your life, and don't try to "cast" other women as your supporting role.
posted by scody at 2:10 PM on December 18, 2007 [4 favorites]

Grow the hell up. Seriously. You're 24, it's about time.

What do I mean, grow the hell up? Realize that your cultivated accent, personality, and manner of dressing are a ridiculously obvious affectation. We all have our insecurities, but do you need to make it so damn obvious?

Try to be the kind of guy that a girl will wake up next to, and not completely regret having done while trashed.
posted by shownomercy at 2:11 PM on December 18, 2007

If you're looking for advice on how to have casual sex, I think you'll be hard pressed to find many useful answers other than lectures. There is no trick or magic incantation anyone can give you that will make women instantly hop into bed (or wherever). You sound like someone who is quite self-aware, perhaps to the point of it becoming counter-productive to your cause. You need to shift your focus from yourself to whomever you are engaging with. Most problems with small talk have to do with listening and phrasing questions. If you listen properly and phrase your questions in such a way as to elicit more than a yes/no answer then there will always be a way to further the conversation.

On the subject of approaching women and the whole "creepiness" thing, most of the time when people refer to someone as creepy it has to do with that person not understanding social customs (i.e. standing too close, overstaying their welcome, premature physical contact, inappropriate gestures or conversation, etc...) Basically, the only way to cure creepiness is to be observant of these customs and not overstep your bounds. People don't like to be bombarded by intensity or over-familiarity upon first meeting another person. You should air on the side of caution and feel out what is comfortable and permitted along the way.

As for the sex part... Raucous sex does not mean that you're treating people like they're less than human, assuming that you're not forcing anything on someone. Raucous sex is just really passionate/feverish sex, and I think you'll be hard pressed to find someone who doesn't, at the very least, fantasize about it. In my own experience, fleeting passion is pretty much what casual sex is about. If you want to "make love to someone" then find a girlfriend. It's kinda unrealistic to be in love with someone you just met and are now in bed with.

For the sake of brevity, I'll just add this: Relax, learn to listen and observe, adjust your behavior organically to the situation, be sincere and direct.
posted by ISeemToBeAVerb at 2:13 PM on December 18, 2007 [2 favorites]

MeTa.
posted by WCityMike at 2:14 PM on December 18, 2007

And for goodness sake, stop approaching women in the subway or on the street.

I disagree with everyone who says this. A guy who seemed relatively normal approached me on the street once for a date, and I might have said yes had the whole scenario been so foreign to me. There's no crime in asking. I would just say don't do it so often that the rejection gets to you.
posted by ThePinkSuperhero at 2:15 PM on December 18, 2007 [2 favorites]

Oh, and don't expect the general public to relate to you. Find ye those enclaves. The girls you'll find in them are likelier to have unusual and derliberate attitudes toward sex.
posted by Ambrosia Voyeur at 2:16 PM on December 18, 2007

The smart girls you're looking for are going to see through the self-absorbed bullshit you're slathering on way, way too thick. They can see the towering ego from miles away (and apparently, so can everyone else here). The less smart girls are just going to be turned off and just think you're weird.

Yet I have, in fact, approached (hundreds?) of women on subways and city streets (mostly in NYC) to tell them them they're gorgeous, and ask them out on the spot

Seriously? You have to stop this and eviscerate whatever line of thinking lead you to the conclusion that this was a good idea. Hitting on strangers in a social environment (party, bar, hell even a bookstore or library might be alright) is largely to be expected. Trying to pick up random women on the street is creepy.

Or, alternatively, cheers on having crafted two humorous fake craigslist ads and one thought-provoking hoax of an AskMe thread.

Seconding that. If this was deliberate, then you *nailed* the character.
posted by Nelsormensch at 2:16 PM on December 18, 2007 [1 favorite]

[a few comments removed, if your only response is YOU SUCK, take it to metatalk]
posted by jessamyn at 2:19 PM on December 18, 2007

You can either polish up your act or drop it altogether.

Everything in your question says you seek to do the former; all my experience says you can be happy only by doing the latter.
posted by jamjam at 2:20 PM on December 18, 2007 [2 favorites]

You think knowledge is an aphrodesiac

One more word to the wise (and this is not snark): if you actually want to impress the literate chicks, you better be damn sure you spell aphrodisiac correctly.
posted by scody at 2:21 PM on December 18, 2007 [3 favorites]

The smart girls you're looking for are going to see through the self-absorbed bullshit you're slathering on way, way too thick.

Speaking as one, You're the kind of guy I used to look for when I was single and hunting casual sex. Becuase your affectations scream "EASY, and maybe DOWNRIGHT INSECURE. APT TO CLING. DON'T GIVE PHONE NUMBER." But, I'd take ya home and nail ya, so, I don't think you're off to such a bad start.
posted by Ambrosia Voyeur at 2:21 PM on December 18, 2007

-- The comments about your "intensity" are a really polite way of telling your to back the fuck off. Keep it up and you'll get a restraining order, or someone's protective and large brother will stuff you into a ventilation shaft. Violating basic social norms is not cool, and will not get you laid.

-- As mentioned above, lose all of your affectations: the fedora, the pinstripes, the faux-accent, the writing style which is half-Heinlein and half-Ann Rice, and the "wacky tales of adventure to amuse and intrigue" -- trust me, they do neither. (In fairness, guys who do the "peacocking" thing that the pickup artist guys talk about do get a certain sort of attention; it's just not always a really great sort of attention. If this is your method, that's cool -- but make it your shtick, not your identity.)

-- If you want to meet and have sex with women, you have to go to places where women want to be met. That means stop harassing women on the street (because really, that's what you were doing, although undoubtedly a few of them were really flattered and loved every minute of it... if not quite enough to give you their number) and start going to places like bars, clubs, parties, cafes ... you know, places where people gather for the purpose of socializing.

-- Most importantly, learn how to read people's social cues and body language. This will have a bunch of results, all good, most of them involving you becoming someone who is great to be around, instead of grating, which is how you are right now. It's ok if this doesn't come naturally to you -- treat it as a foreign language, or an anthropological exercise. Watch people around you in every social interaction; go to bars and cafes and be the fly on the wall; study what is going on until you get it, and then start trying to apply what you have seen to your own behavior.

-- You say you don't drink, and that's cool. But a really good skill to learn, that will serve you well for the rest of your life, is how to nurse a beer for a whole evening. Think of it as protective coloration -- you look just like all the drinkers around you, and you don't have to have all those socially disruptive "why I'm not drinking" conversations every five minutes ... and yet your total alcohol consumption over four hours might be a third of a bottle of beer. Disregard this if you are a recovering alcoholic, or allergic to alcohol, but even then there are bar drinks (eg soda and lime) that look like "real" drinks and serve the same function. Along with the beer-nursing, you should learn basic bar-skills -- how to elbow your way in and order a drink at a crowded bar; when it's your turn to order a round (even if you are still nursing your first beer); how to talk with strangers.

Basically, I disagree a bit with the good HMSBeagle, and think that lots of women are happy to have casual sex... but they aren't having it with men they literally meet on the street. They are having it with men they meet in seemingly safer locales -- online, in bars, at parties, etc. And they aren't having casual sex with guys who use phrases like "women I've been lucky enough to somehow bed" or who act like socially inept weirdos. If I sound harsh, it's because your post reminds me of myself when I was 16 and no one wanted to sleep with me and I couldn't understand why not.
posted by Forktine at 2:25 PM on December 18, 2007 [4 favorites]

Read all this.
posted by fire&wings at 2:26 PM on December 18, 2007

Okay, yeah. Maybe lose the fedora but I still liked the ads.
posted by otherwordlyglow at 2:37 PM on December 18, 2007

this is a crazy question, but here you go:

1. be confident. at all times. it's stupid, but it's the cardinal rule.
2. go to bars. plenty of people go to bars to loosen their inhibitions a bit. they do this for a reason.
3. get them drunk. don't take advantage of them but get them drunk. don't try to make them drink if they don't want to or anything but if they're willing to have drinks bought for them, do it.
4. lose the hat.
5. don't talk about yourself all the time. ask them questions, and ask followups to their answers.
6. lie your ass off. everything they say is fascinating.
7. be nice to their friends. don't ignore any of them, and especially be kind to friends of theirs that you might think are unattractive or who seem to get less attention than the others.

I dislike questions like this because you're asking for formulae that apply to "getting casual sex" and people, depressingly, may work that way (at least, more often than I like to think about) but exploiting that fact is manipulation. so the advice above is likely decent for accomplishing what you've described, but it's not really a great thing to do.
posted by shmegegge at 2:41 PM on December 18, 2007 [1 favorite]

Women like to sleep with guys who make them feel like the most fascinating person in the room.

Women don't want to sleep with you because you so clearly find yourself the most fascinating person in the room.
posted by MsMolly at 2:42 PM on December 18, 2007 [21 favorites]

eau de asshole my holy water

oh yuck.
posted by changeling at 3:00 PM on December 18, 2007 [1 favorite]

I am chuckling ebulliently in close proximity to your person as I devour hungrily your delectable word salad. Kudos. Seldom have I guffawed so heartily while perusing the persistently pithy pages of the Emerald. Truly, huzzah and godspeed.

I say this with love - and I am beautiful, thanks for noticing - you're hilarious. You are. You obviously have a great imagination and I have a sneaking suspicion that you want to be a writer. Some day you're going to pull it all together but, for now, I would focus on two things:

1.) Listening.
2.) Saying what you mean.

Women are smart and some of us would bone you if you'd shut it, let us get a word in edgewise, and come to the point when it's your turn.
posted by TryTheTilapia at 3:01 PM on December 18, 2007 [14 favorites]

eau de asshole my holy water

oh yuck.

yucky indeed, not to mention that the proper French is actually "eau d'asshole."

on preview: my girlcrush on TrytheTilapia just grows by leaps and bounds.
posted by scody at 3:10 PM on December 18, 2007

Go find and rent The Pick-Up Artist. There's a scene in it where Robert Downey, Jr. finally gets to have sex with Molly Ringwald, but can't stop talking while they're doing it. Finally, she says something to the effect of, "If you can just shut up for one second, I'll come."

There's a lot of wisdom in that scene.
posted by mkultra at 3:12 PM on December 18, 2007

Man, you don't seem that bad to me. Quite the beat-down you're getting in this thread. To me, you seem like a neat kid -- a little awkward and a little deaf to how your tone will be heard, but funny and interesting and kind of goofy. My conversational style is in the time-honored tradition of Gozilla? "I'm looking for my Mothra"? That shit cracked me up.

The pros list in this question is the part that really comes off as a bit wanky. We do not care about your fabulous accent. The ads, I actually mostly like. I think you're going to get a lot more friend responses than sexy responses out of them, however. I think a gal who likes the ad is going to laugh, and think "I'd like to hang out with that guy." As much as you say you're just looking for a casual sex partner, you're clearly advertising for someone who meets your standards for Something More -- and being pretty particular about it. Your casual sex partners should not have to pass a pop-culture quiz and win a spelling bee to get in the sack with you. They need not quake before the fires of your rhetorical brilliance.

You want someone who is smart and not afraid to hide it, has a quirky sense of humor, and who wants to get laid. Sounds good! But you're writing like you're laying down a gauntlet, not issuing an invitation.

You definitely need to Tone. It. Down. as everyone has been saying. Along the lines of another poster's suggestion, something like "occasionally charming geek with a penchant for conversational hijinks seeks same for sexy hijinks" should work fine.

Forget the approaches on the street -- as others have commented, not only does it have a high creepiness factor, but you're setting yourself up for failure. You could be Captain Fabulous and still not get a good response ratio with that tactic. As a lady, I add my voice to the chorus asserting that many ladies do not care for it. Occasionally we may appreciate the brief compliment, but I am unlikely to just up and go for a date with a stranger who approached me that way. A date is a high-pressure one-on-one situation -- you don't want to put yourself there with someone that you know nothing about other than what they look like and that they told you you're physically attractive. It could be 30-60 minutes of pure awkward! At best! If you have a friendly conversation with someone for a few minutes (and establish that you can speak relatively easily to each other and maybe have something in common) and then say "hey, would you like to meet up sometime?" THAT will go so so so much better than "you're pretty, can I have your number?"

Hope some of the feedback here is helpful for you, and don't take it too hard. Despite some of the more vociferous replies, this is really a response to how you come off, not who you are -- just try to learn how to read the room, and what you might be read as vs. what you intend.
posted by tigerbelly at 3:14 PM on December 18, 2007 [3 favorites]

First, I think you should ditch the European accent. Chicks are more likely to bed you if you have a Jamaican accent.

Second, trade the Fedora in for a Homburg. It's a little more classy, and that is the look you should be going for to fit your style.

Third, drop the pinstripes for a nice houndstooth. It will make you seem a little more warm and less aggressive women dig that.

Other than that, keep up the rest of it and you should be fine.
posted by dios at 3:27 PM on December 18, 2007 [4 favorites]

The people I know who have been most successful (sexually speaking) - and they're not by any means rich or gorgeous - have gotten there by being genuinely interested in other people. They ask questions. They listen. They demonstrate that when they were not talking, they were paying attention - like, they remembered that you mentioned an interest in Subject A, and the next time you meet, they've brought you a book or something about Subject A.

You can be ten kinds of witty and smart and sophisticated, but if you never let your date get a word in edgewise, and you demonstrate that you don't pay attention when you're "listening", you'll rarely get far in the making of the sex.
posted by rtha at 3:45 PM on December 18, 2007

Holy crap. I thought everyone was overreacting and then I clicked those Craiglist ads. Dude, really. Just tone it back a half dozen notches. I'm pretty damn sure you're makin the geeky girls go "Whoa, even I'm not that desperate." I'm sure you are a cool guy and lots of girls appreciate men who read and are intelligent but the way you're coming across is overwhelmingly smug.
posted by CwgrlUp at 3:47 PM on December 18, 2007

Your problems have been covered in detail, so here is some practical advice. If you want to end up being the kind of guy who can dress sharp and talk snappy without people saying "Lose the fedora, motormouth," you need to earn it. A 24-year-old cannot have the life experience to back this kind of behavior up, and I mean by definition. It has to have come from other sources: books, movies, whatever. And people can sense this. Put bluntly, you're a cosplayer, accent and all. And cosplayers only get laid at anime conventions.

What you need to do is tone it way down (as people have said) and live a rich, interesting life. Wanderlust helps with this, but only if you make a serious effort to relate deeply and humbly to the places you go. Let them change you. Let them remake you into a real man of the world. Learn the language -- I mean really learn it -- and enjoy the effect this has on your attitude to language in general. Experience the culture as what it is, not as a set of differences from the culture you grew up in.

Do this for years, not months. Remember to keep it not about you all this time.

You will gradually become the intriguing, unique, magnetic man you clearly long to be. It's a long-term project. But it will be worth it. You won't have to try so hard to be different -- your experiences will have made you that way. You will have fascinating stories to tell about things other than yourself. You will dress better, and not just because you will own flattering clothing from around the world. You will be real. You still won't be able to have casual sex with any attractive single woman you like, but you'll be in a much better position to attract women in general. And, to be honest, you probably won't care as much about casual sex any more, because you will be too busy leading your marvelous life.

(Who knows? Maybe you will even have accumulated the necessary je ne sais quoi to pull off that fedora. Try spending a lot of time in Europe.)
posted by No-sword at 3:50 PM on December 18, 2007 [10 favorites]

You want to have more casual sex?

1. Affect a little more masculinity. Watch how Ryan Gosling works his magic in the early parts of 'The Notebook'. You need a little Bear Grylls in your life.

2. If your good looking, you should not be approaching women cold. Find places where prolonged eye contact is possible and not creepy. Plenty of women will non-verbally give you the green light to approach ( Frequent glances are not hard to read ). Never approach without a green light. Get in, procure a phone number / email and get out.

3. Redefine the timeline and effort required to go from stranger to casual sex. The more time you invest in each person, the more likely you will be to have casual sex. You can also multi-task. Let the women know you are multi-tasking. In some cases, it will counter-intuitively work to your advantage.

4. Affect a little mystery, vulnerability, and aloofness.

5. Never forget this quote: "When I was with Gladstone, I thought he was the most fascinating man in the world. When I was with Disraeli, I thought I was the most fascinating woman in the world."
posted by kaizen at 3:50 PM on December 18, 2007

I consider myself an intelligent female, so I hope that you find some wisdom in the following. (On the other hand, I found my husband via Internet dating, so you might need to take this with a grain of salt if you're only looking for casual encounters).

My first impression when reading both your post above and your Craig's List entries was that, despite all that wonderful language, I didn't get a feeling for who YOU really were. I got the feeling that all those clever words were not used for exposition, but for concealment. Now, I'm all for leaving a bit of mystery in a relationship (although I myself am a "heart-on-sleeve, this is who I am" sort of gal). But I walk away from reading you with only one impression: "I have a sense of style". And intelligent women, even those who like casual sexual encounters, aren't looking for an arm ornament. Intelligent women tend to like intelligent men, and women are attracted to men by something other than mere looks (or at least so says John Gray)

The impression I am getting from your note is a lot like the impression I used to have of my now ex-husband's father. He was a Type -- well-dressed, urbane, cultured. But that was ALL he was, or at least all he let anyone know about. To me, he seemed like a well-designed animatron. It's a pity, because I think there was a real person under there. And I think the same thing about you. But you're not giving me much of an idea of that real person.

It's not the fedora or the pinstripes that make or break you -- it's what's underneath.
posted by lleachie at 3:54 PM on December 18, 2007 [4 favorites]

Read in bars. Don't talk to folks without them talking to you first. Don't 'show off' what you're reading. Just read a book you like in a bar. You'll have to learn to drink, but that's okay, you can drink slow. Because you'll be inside, you can leave the fedora at home (manners), as well as the fake accent (don't lie to people).

Your mission in the bar, while you read, is to observe the flow of people around you. People will be talking and interacting, having fun, being approachable, normal. This is what you want to emulate! You can be the smart, witty fun guy and still be normal. The fedora-accent-pinstripes thing? Save that for a fancy-yet-ironic third date.

As you read, eventually, you will be brought into conversation with those around you. This will be a test. Can you pass for normal? Can you still be the soul of wit without your costume? You probably can. So work it, even if it's just faking your way through talk about sports.

After you have done this enough, you will have developed an approachable, likable, witty persona. This is the persona you use to talk to women on the train. Guy in fedora and pinstripes hustlin up to women and telling them they're beautiful? Steve Martin and Dan Ackroyd did that bit years ago. Good looking funny guy who can share a moment with some random cutie in cat's eye glasses? That takes work!

Remember that your, er, 'prey' is the librarian stereotype. I'm a librarian and I know this type quite well. Nothing puts them off like ostentatiousness, nothing warms them up like a wry observation.

And who knows? If you read in enough bars, you may find a girl who is reading the same thing too.
posted by robocop is bleeding at 4:02 PM on December 18, 2007 [8 favorites]

robocop is bleeding is a very approachable, likable, witty person. Take his advice and tattoo it on your skin.
posted by ThePinkSuperhero at 4:08 PM on December 18, 2007 [1 favorite]

Take off the fucking fedora and find yourself a hunting cap. It must, must be green. Ahhh there now. Suddenly you're Ignatius J Reilly from A Confederacy of Dunces. Do yourself a favour and go read it. I'd call hoax but sadly share your weakness for needless oververbification - and the fact that I can't tell whether this is real or not should tell you where your problem lies. My advice? Quit the chicks and focus on your writing. You're a kook, but you've got some talent.
posted by bookie at 4:24 PM on December 18, 2007 [2 favorites]

To be a really good writer, you must be a good editor. Write your ad, then leave it for a week, then cut 75% of what you've written. Leave it for another two days, and cut more.
One charming thing = what a charming ad.
Fifty charming things all piled on together = too much, what's this guy's problem?

Also, n'thing the advice not to expect dates or sex from just approaching women at random on the street. No way. Even if you were attractive and charming and more, I wouldn't agree to a date after that -- it's just too weird. And I would be smiling as I told you I was already attached, because I would feel awkward as hell about the whole situation, and I smile when feeling awkward.
posted by LobsterMitten at 4:28 PM on December 18, 2007

If you weren't about 15 years too young, I'd swear you were someone I once knew, down to the fake (ala Madonna) accent and the fedora and, almost verbatim, your way of presenting/viewing yourself. It's downright uncanny. (I haven't even clicked on your craigslist ads; just the first 3-4 paragraphs of your question was enough.)

That means I suspect other women are also pegging you as a "type" they've encountered before instead of a unique and fascinating bon vivant-- and that type is, "pathological narcissist."

That's much more creepy than, "unable to make small talk", and if it's not true to who you are you need to figure out how to knock it off, stat.
posted by availablelight at 4:35 PM on December 18, 2007

If you really can dance then you should have no problem getting laid. So I have to suspect you're simply a victim of bad taste. In dress, in tactics and definitely in women. It's understandable. You're young and sheltered life and have only been exposed to a few types.

So change things up.

Rather then wearing pin stripes try something a bit more laid back. Most guys cannot pull of pinstripes: it takes broad shoulders, long legs, and an easy confidence. You can still dress classy and distinguish yourself every other is-this-business-casual?-I-desperately-need-a-wife-to-dress-me dork out there. The three S's -- a nice shirt, nice shoes and a nice smile -- will go a long way.

When you speak to women you shouldn't be trying to impress them. No matter how impressive you are you will always come off as desperate. Instead of telling women they're gorgeous (always overkill) just tell them that you like their smile. Instead of offering up some overwrought, "ironic" joke try simply making a silly face instead. Your goal isn't to wow the lady into submission but to make her feel good and get close to her. Pouring on compliments will actually drive most people away.

And, seriously, stop aiming for boring, "nerdy girls" and start broadening your horizons. A lot. There are plenty of women out there who would appreciate a fun loving, intelligent guy who's not afraid to look silly. You're filtering them out because they don't listen to indie rock or wear stupid, blocky hipster glasses and this is a terrible mistake. I assure you, they might not be the exotic, Plain Jane geeks of your dreams but they have their strengths and are wonderful in their own way. Take a risk and learn to appreciate beautiful women of all shapes and sizes. Stop obsessing over some silly "Bookclub Goddess" and take a long look at the many, many lovely women out there whose idea of a good time isn't crochet.

And, really, there's nothing wrong with hooking up on Craigslist. Do whatever works and whatever's fun. Don't let the bullshit opinions of others stop you from having the time of your life.
posted by nixerman at 4:36 PM on December 18, 2007 [1 favorite]

I kind of liked the line, "If I were to shake hands with a frat boy, we would both explode."
posted by jayder at 4:47 PM on December 18, 2007

You know, I'd rather someone err on the side of "trying too hard" than "not trying at all." You'll figure out what works and what doesn't work through trial and error anyway, and that's what this post is about, right?

Mm, now, as a 20-something female, I think I'm qualified to suggest...

- Cut out anything that even implies "your IQ has to be this high to ride." No one wants to go out to coffee expecting to get judged on their IQ. The smarter a chick is the more she's likely to say, "I hardly know anything about anything" anyhow.

- nthing self-deprecation. It's a bit below-the-belt, but self-deprecation generally makes other people wanna go, "Aw, you're not so bad." It's sneaky. Done right, it's brilliant.

- The people I've had NSA sex with are all people I have known for, mm, at least long enough to feel that they will be honest with me about STDs and will work with me on the baby-preventing front. Either I've initiated or we just kinda fell into a drunken heap together - when the other party initiates, I have no problem rejecting him, because I'm female and cute, and there will never be a shortage. So you have to catch her in the right mood, essentially, and learning to read people will help immensely with figuring out feminine moods. This is not an innate ability you're either born with or not. It's a cultivated skill. So go cultivate it.

You might find it worthwhile to cultivate many female friends. They don't have to be close, and you don't have to see them but once every few months or so, but during that time, you need to show you're trustworthy, and so long as they understand you're available and interested, you'll be on the "considered" list when she wants to tumble.

The addendum to that is anyone who's willing to step off the street and into the bedroom with you, a person she doesn't have any references for, puts an undue amount of trust in you. Her reasons for trusting you to this extent may be either benign or pathological, but unless she is a simple country girl from some small town where there's no crime, you should probably consider why she may be willing to put so much of herself in the hands of someone she hardly knows.
posted by reebear at 4:55 PM on December 18, 2007 [1 favorite]

You're trying too hard, way too hard, but your main problem is that you're working very hard at pissing in the wind. Finding a pool of women who want to fool around with you is a lot like writing good fiction: show, don't tell. Again: don't tell.

I'm female, but I think my advice transfers well to those of the weaker sex, too. I'm incredibly dorky and shy, but when I was single, I always had plenty of suitors. The things you like, or the things you say don't make you attractive; it's the things you do.

Your ads and your question make you sound like a dork, because you're presenting yourself in a dorky way, but underneath that, you sound like a very intense person gifted with a lot of creative energy. Channel that energy into doing something that you love that will put you out in the world. If you play an instrument, join a band. If you don't play an instrument, learn one. If you like riding your bike, start racing. If you make art, pursue it more seriously. If you like to write, start attending poetry slams. Humans are mammals, and members of our specie have done millions of wonderful, powerful, worthwhile things because either consciously or subconsciously, we hope that whatever we're doing will get us laid. Picasso, Jimi Hendrix, Buckminster Fuller and Ben Franklin have one thing in common: they were never called assholes.
posted by freshwater_pr0n at 5:34 PM on December 18, 2007 [1 favorite]

IANArepresentative case, but I was a nerdy girls with a healthy interest in casual passionate sex in my 20s and 30s, and here are what I see as the key problems in your case:

1. Online advertising has killed all the joy of casual hook-ups. Good casual sex is all about immediacy and chemistry and clicking whereas Craigslist and OKCupid and all that are about auditioning, making what amount to cut-and-dried "appointments to fuck" and otherwise removing all the ineffable, unpredictable ambient vibe-iness and mystery of catching someone's eye "across a crowded room." I know you're trying to be efficient and maximize your chances to score, but that, my friend, is fratboy behavior and therefore a turn-off.

2. You don't sound as if you like sex much. Maybe you do actually like sex in reality, like reveling in it and getting all sticky and all that, but your post here and your ads don't sound that way. You sound like someone who is, with elaborate calculation, trying to say what he thinks women want to hear in order to give up the intercourse.

3. On a related note, the "narcissism" problem is not so much that you sound as if you're in love with yourself, but, more critically, you sound as if you're clumsy and selfish in bed, and that is a real dealbreaker. Women with a healthy interest in proficient, meeting-of-equals casual sex can smell that attitude a mile away, and after you've boned a couple of guys like that, you give the rest a wide berth. By the way, it's equally selfish and narcissistic to pull the (no offense to Mefites of similar name) "Ladies, I sure do love the cunnilingus" routine, where you make a big, flamboyant "Tell me vhat you vhant" dramatic show about taking great, self-sacrificing pains to pleasure us, Mandingo. It's fake and all about gaining accolades for yourself. Anyhow, not that you DO any of that, but your persona definitely creates that impression.

4. You don't sound like someone who can hold a real, smart, off-the-cuff, funny conversation, even a little (charmingly) tongue-tied. Your shtick sounds rehearsed, like a person who is not at ease in his own skin. If you can just sit for a couple of minutes and have a real, unscripted, sometimes halting, give-and-take conversation about things other than yourself, in a way that doesn't seem like a self-aggrandizing pop quiz, you'll be much more compelling to women.

Obviously, tastes vary greatly, but guys who genuinely enjoy sex (not just ejaculation or ego-stroking), who genuinely like women, who can appreciate women that feel the same way and not be all neurotic or clingy or moralistic or weirdly distant but can be real (if very short-term) fuck buddies -- those guys positively smolder. They're magnetic, regardless of looks. Whether or not they would follow through, plenty women think about taking those guys out to the alley (literally or figuratively) and doing divinely filthy things.
posted by FelliniBlank at 5:45 PM on December 18, 2007 [9 favorites]

Write shorter personal ads. Be as weird as you want to be but keep it short. Ask a specific question in your ad. You are doing fine. Maybe your annoying I don't know I've never met you. It is less that you are full of yourself or trying too hard than your expectations are too high. Have expect to know a woman for at least a few hours of not watching a movie before she has sex with you. Show her you are attracted then relent and let her grow comfortable. Then ask her to see your etchings or whatever.
posted by I Foody at 5:46 PM on December 18, 2007

There are a lot of good responses here. One thing that confuses me though, I keep reading all the ladies saying that there are few girls who would have NSA sex with a stranger. This surprises me. I have been out and about plenty and have found no shortage of females desiring nothing but a one-night stand. One trip inside a dance club catering to the 21-35 age group should prove that to be true. I have also lived many places and have traveled quite a bit, and there doesn't seem to be any geographical explanations. Don't get me wrong, I don't always leap at the chance for casual sex, but I also can't claim to have been a perfect angel either. One thing I do agree with is the safety issue for ladies. While what I have written is true, I have no understanding as to why so many seem willing to be with people they don't know at all. It's surprising and not the least bit comforting when thinking of it from the point-of-view of reality, crime and knowing that yes, it can, "happen to you". I think maybe what a lot of the posts from the MeFite ladies show is that they are smarter, and have smarter friends, than society at-large. At any rate, it's been an interesting discussion.
posted by Gerard Sorme at 5:54 PM on December 18, 2007

I am a woman and I endorse FelliniBlank's answer.
posted by desjardins at 5:55 PM on December 18, 2007

I fit most of what you're looking for; you fit most of what I'm looking for, too (well, aside from the pinstripes, fedora, possibly affected accent, and occasional misspellings). But if I was bored enough to browse Craigslist, and came across your ad, I'd leave it open in a tab for a couple of days, but I'd never e-mail you.

I'd look at the ad a couple of times, but every time I'd think, "This guy sounds pretty cool . . . but every sentence of my e-mail would have to be crafted over the course of hours. He's going to be judging the hell out of me, and I'm going to have to be killing myself to prove I am, really, I swear, smart. If I include one sentence that isn't jam-packed with offhanded obscure references and try-hard comedy, he's going to delete my e-mail immediately."

Let me guess -- your fan mail is mostly one-liners? "Lol, you sound like such a cool guy"? With what you're giving us, that's the only other route to take.

I like people who are smart, but not so desperate to prove it -- and who won't make me work so hard to prove my intelligence. To put it differently, on one hand, there's using whatever words come naturally; on the other hand, there's trying to shoehorn the biggest words you know into your first-date conversation, and staring across the table to detect every nuance of the girl's response. You sound like the latter guy. Don't be that guy.

PS. Craigslist? Wrong, wrong venue, at least if San Diego is anything like New York. If you do want to meet people online rather than IRL, at least opt for a site like OKCupid.
posted by booksandlibretti at 5:56 PM on December 18, 2007 [2 favorites]

One thing that confuses me though, I keep reading all the ladies saying that there are few girls who would have NSA sex with a stranger. This surprises me. I have been out and about plenty and have found no shortage of females desiring nothing but a one-night stand. One trip inside a dance club catering to the 21-35 age group should prove that to be true.

Right. I think the issue is not that it's so terribly unusual for women in that age range to be potentially interested in NSA sex; what's unusual is to engage in it when approached the way the OP seems to be approaching women.

Back in the day (read: grad school), I engaged in NSA sex more than once (caveat: I went to grad school in, like, the Jazz Age, when not only was there no Craigslist, Craig wasn't even a twinkle in someone's eye). Guys I was casually friends with and could be fun, friendly, low-maintenance, hot fuck-buddies? Sure. Good times. A couple of flings with guys I'd met in a bar and engaged in mutual repartee (usually involving modernism and Marxism, my weaknesses of choice in my 20s) over whiskey? Ah, sweet, sweet youth! But some guy in a costume who walked up to me on the street and asked me out? NEVER.

My point is, yes, there's absolutely a safety issue for women in regards to casual sex. But guys we get to know more organically, as it were -- guys we're friends with who turn into fuck-buddies, or guys we initially meet in social settings like bars or cafes and wind up having some immediate chemistry with -- are, broadly speaking, less likely to set off the OMG POTENTIAL WEIRDO RAPIST KILLER alarm than a stranger who barges up to me on the street to announce that I'm gorgeous, or His Ironic Hipness nattering on painfully about himself in a personal ad.
posted by scody at 6:14 PM on December 18, 2007 [3 favorites]

less likely to set off the OMG POTENTIAL WEIRDO RAPIST KILLER alarm than [...] His Ironic Hipness nattering on painfully about himself in a personal ad.

Actually, on second thought, the His Ironic Hipster schtick wouldn't make me suspect he's a rapist; it would just make me think he'd be aggressively judge-y and self-satisfied on a date, and thus No Fun in Bed. But harrassing me on the street pretty much always gets an OMG NO gut reaction.
posted by scody at 6:30 PM on December 18, 2007

I'm young (24),...the dozen+ women I've been lucky enough to somehow bed,

Dude, you're doing better than most (assuming mere quantity is your goal) (and don't ask me how). What exactly were you expecting?
posted by jonmc at 7:14 PM on December 18, 2007

Women like to sleep with guys who make them feel like the most fascinating person in the room.

Women don't want to sleep with you because you so clearly find yourself the most fascinating person in the room.

eh, it's not that simple... I mean first of all, different women like different things yadda yadda, but more to the point, a woman who is being told she is the most fascinating person in the room by some little annoying kid is not gonna be turned on by it. And plenty of women will be turned on by a guy who genuinely is an interesting person, even if he happens to kinda know it too. "being made to feel" fascinating is a kinda lame idea, really. I think everyone likes those people who actually bring out the best parts of ourselves - if we actually become more interesting people by spending time with them, then we are in a sense "made to feel fascinating" - but not because some boring guy just thinks we're so cool. That can just be annoying if you don't feel the same way back.

As for this, if all you're looking for is one time casual sex, you are doing too much talking. If you want fuck buddy type sex, then you can do that much talking, but as friends, and if you end up having sex, yay, but enjoy the talking for its own sake rather than as means to an end or you're basically being a dick. If you really just want to get laid, talk less.

You basically just come off sounding young and not fully at home in who you are yet, so a little too focused on the, what you might call trinkets of personality... If you really love fedoras, wear one. Wear it because you love it and it means something to you and it is genuinely part of who you are. If that is the case, you won't mind that people will think it's cheesy or cliche. Not dorky - dorky is not an insulting adjective anymore, so you can't be self-deprecating by saying, I know, I'm a dork - you have to choose an adjective you actually think is insulting. But if you're just wearing it because you think it fits a certain offbeat, erudite vision of yourself you have, then drop it. Not because it's cheesy and cliche - which it is, but that's been covered and anyway isn't that important - but because you're trying to fit a vision you have of yourself instead of finding out who you actually are when you relax and don't have hats and accents to separate you from the next guy. Maybe you're thinking you're trying to get laid here, not make new friends, but really being comfortable with who you are is the root of confidence, and confidence is almost always a good start for picking up women.

One other thing: I don't think asking women in public is creepy - unusual, but if done in a friendly, non creepy way, I wouldn't think creepy. Also, he said it never proceeded past a coffee, not that they were never available at all. And, I would bet a high percentage of women past a certain age are "taken", if they're not at a singles bar or whatever. Most of my friends are most of the time, etc.
posted by mdn at 7:20 PM on December 18, 2007

It's my experience that people tend to say, "You seem really intense," when what they mean is, "You seem really insane."

Like availablelight, you sound uncannily like somebody else I used to know. The international bon vivant schtick didn't work for him, and it's not going to work for you. Quite the contrary.

My small chunk of advice: keep the fedora or the pinstripes or neither but not both. (Never both. No.) Then practice walking around as if you had no idea that your fashion sense were anything unusual. Forget that you are anything but Joe Ordinary. Take a vacation from this carefully crafted image. Work hard if you have to. You can tell from previous answers that a wide swath of people find your image predictable and annoying, so it's time for a new way to behave.

Look, interest is really just a heightened form of curiosity. But you're not providing anything much to be curious about. You're tremendously peggable and therefore dismissable. If you must wear a fedora, make it a little interesting: behave in other ways as if you were not the kind of guy to go around with a fedora. I promise you, the contrast between a fedora and a down-to-earth attitude is vastly more intriguing than wacky tales of adventure.

And getting more down to earth will help in other ways, too. What does a woman want from casual heterosexual hedonism? Well, one thing she wants is to know is that there will be no tedious and uncomfortable drama: the guy won't suddenly fall down the "emotional rabbit hole" all by himself. He isn't going to decide that he loves her truly and therefore will go pester her with flowers, "witty" letters, and late-night guitar songs under her window. Despite what Hollywood might say, that kind of thing is no fun at all. You come across as pretentious and needy; both of those make you look like a guy with a better than average chance of becoming Drama Boy. Bad news.
posted by sculpin at 7:29 PM on December 18, 2007

Speaking as one, You're the kind of guy I used to look for when I was single and hunting casual sex. Becuase your affectations scream "EASY, and maybe DOWNRIGHT INSECURE. APT TO CLING. DON'T GIVE PHONE NUMBER."

It amazes me that girls would worry about how "easy" a guy was. I mean, studies actually show that like 90% of men would agree to have sex with an unknown woman.
posted by delmoi at 8:04 PM on December 18, 2007

On further reflection, Anon, I fear I've been a little more snarky than helpful... assuming this question is sincere, what really seems to be going on here is, as mdn posted, a kind of fixation on the "trinkets of personality." I think that's what everyone is really reacting against. But I get it, in a way: I remember back when it seemed ("seemed" being the operative word here) like everything essential about me really could be boiled down to my book/record collection, and my vintage clothes, and my obscure interests -- and, therefore, that it was reasonable to view others by the same matrix.

But our books/records/clothes/hobbies/etc. are really nothing more than preferences -- they might provide fodder for conversation (and there's nothing wrong with that), but at the end of the day, they don't say anything terribly meaningful about who we are. This might sound weird, but in a very real way, they're not truly important. You know? I mean, lots of assholes have had adventures backpacking across Thailand, while lots of spectacularly warm, funny, smart, sexy, fascinating, worthwhile folks have never been out of the lower 48. It's really our qualities that matter. Kindness, compassion, wit, and generosity (for example) are ultimately far more essential about who someone is than whether or not they can discuss Laszlo Moholy-Nagy's career at length or have all the Mekons singles on vinyl.

The kind of person you are, Anon -- as a son, a friend, a partner, a brother -- is actually far more impressive and interesting that the cut of your jib or the arcane pop culture knowledge you possess or your SAT scores. But what's coming across, in your way of characterizing yourself and the women you seek, is pretty much the opposite -- and that, as I said, is why I think most of the responses here have been so strongly along the lines of "tone it down, fancypants" rather than "goodness, how charming." Who you are is much more than an agglomeration of "impressive" or "interesting" quirks, styles, and preferences set forth in self-aggrandizing fashion. Start relating to yourself both more humbly and more authentically at the level of qualities rather than quirks, and see if the way you relate to women (and to other people in general) starts to change, too.
posted by scody at 10:43 PM on December 18, 2007 [33 favorites]

I think you need to find somewhere that girls are more open to being hit on, where you won't feel ashamed of having picked them up - you know there's a range of places between 'on the street' and 'sex parties'? If you really want to pick up, you might need to suck it up and start going to bars (I don't know, maybe clubs will do). You don't have to drink, just be there. As a girl, I'm almost definitely not going to respond positively to a guy asking me out on the street, but that same guy who's sober enough to have an interesting conversation at a bar that night? Chances are waaaay higher.
posted by jacalata at 12:13 AM on December 19, 2007