What happens on a date?

February 3, 2008 7:14 PM

I'm a 26-year old straight male, and for a variety of reasons I have never been on a date. I would like this to change, but I'm at a loss for where to start. I'm particularly nervous about what to do on a date, especially given my absolute lack of experience. What should I expect, and how can I get over my fears of coming across as romantically/sexually naive?
posted by anonymous to human relations (63 answers total)

Start by asking someone out, of course. The best thing you can bring on a date is your listening skills. Be polite and engaged, and genuine.

Remember that compatibility is a crap shoot and if things don't work out don't take it personally. Just move on and ask someone else!

how can I get over my fears of coming across as romantically/sexually naive?

Realize that you are not the only inexperienced person of your age. I know many people who went through college and beyond without dating at all. It won't put a good woman off.
posted by red_lotus at 7:19 PM on February 3, 2008

Don't think of it as A Date (DATE OMG SCARY!). Think of it as spending time with someone you like, to see if you want to keep doing so.
posted by ThePinkSuperhero at 7:20 PM on February 3, 2008 [5 favorites]

I would like this to change

This is a good start. You have to do three things: try, try, try again. It is very unlikely that you will be able to "close" with your first dates due to your lack of experience.

Take this as starting points:


Tony Layguide
Hey I learned my game from this guide in the end of the 90ies.

A guy "called Mystery" who posted a lot on the Usenet in the 90ies has become a celebrity now. He also wrote a book "Venusian arts" but I could not find it immediately on Amazon.

Start with Tonys Layguide, get a wingman and train train train. It is all a game. Trust me.
posted by yoyo_nyc at 7:25 PM on February 3, 2008

It might be helpful for you to tell us the various reasons why you've never been on a date.

The internet can be a place to find a date quickly, just to get it over with.

Your first date might be really fun, or might really suck. It would be good if you prepared yourself for that and realized that that might not have anything to do with your lack of experience (i.e. people who have dated a lot have sucky dates and great dates).

I think what you get out of a date, particularly the internet kind, is the chance to meet someone and hear about their life. That's about all you can expect. It can be kind of fun. It's a good excuse to do fun stuff. Like take a walk. Dinner dates can be more stressful, IMHO.
posted by sully75 at 7:26 PM on February 3, 2008

You could do worse than reading this site, and ignoring any advice of the "how to pick up chicks" variety.
posted by shadow vector at 7:42 PM on February 3, 2008 [1 favorite]

How do you overcome your fears? Realize that everybody is as human as you are, and are therefore probably are nervous as you are. So just treat the date as a friend, hang out with them. To flirt, touch them (...appropriately, i.e. the arm over the shoulder, touch her arm lightly as you speak to underscore points), laugh, smile.

Breathe.

And most importantly? Ask out a nice girl. The first date is the hardest, especially if it's your first date ever.
posted by flibbertigibbet at 7:51 PM on February 3, 2008

Why not just do something you'd normally like to do, but with someone rather than by yourself?

If you dial down your expectations, you'll relieve your stress and maybe actually have a good time, regardless of what does or does not happen.
posted by SPrintF at 8:00 PM on February 3, 2008 [1 favorite]

Ugh. I am a big non-fan of the pickup artist / layguide stuff. It just seems very sleazy to me.

The biggest thing to remember on a date is LISTEN. It's okay to talk about yourself a little, but it's easy to just keep talking, and talking, and talking ... and before you know it, you've monopolized the conversation and bored your date to tears. That's not good. Talk a little, ask open-ended questions if the conversation stops, listen a lot, have fun.

Find someone whose interests you share, ask them out, and just enjoy a meal or some other activity with them. That's kind of the whole concept of a date.
posted by Kadin2048 at 8:02 PM on February 3, 2008 [1 favorite]

Oh, God, please don't start your dating career with the pickup artist stuff. Presumably you would like to date in order to meet some new women and have fun, not in order to get as many notches on your bedpost as possible.

I've dated a lot and I don't think there are any real hard and fast "rules" for dating. It's easy to think that everyone else knows "how" to date and you don't, but it's very variable among different subcultures, cities, and age groups. If you're a geek interested in dating geek women, you might want to just get together with a girl and play videogames or go see a book reading. If you're more of a professional type, dinner and drinks or dinner and a movie are classic. But the first step is finding a girl that you're interested in and asking her if she'd like to do something sometime. My one useful piece of advice is that asking someone if they'd like to do something specific is much more impressive, and much less likely to get shot down, than a vague query.

For example:
Philosophygeek: Hey, I saw that Persepolis is playing at Ye Olde Art Theatre on Thursday. I heard it's great.
Girl: Yeah, I've been wanting to see that.
Philosophygeek: Want to come with me? We could go to that Vietnamese place on Main Street beforehand.
Girl: Sure!

This approach shows confidence, something about your tastes (whatever they are), and the ability to plan, all of which are attractive qualities. Dates where you do something (like going to a reading at Barnes and Noble or checking out an unusual restaurant) are also good because then you have something to talk about besides "So where'd you grow up?"
posted by alicetiara at 8:10 PM on February 3, 2008 [1 favorite]

Yeah, I'd take the "it's all a game" stuff with a grain of salt. Think of a date as having coffee with a new friend, but with potential extra sparkiness. You might be interested in continuing the conversation (and more!) or you might not. The date doesn't have to be some big pressured ritual thing - you could go for a bike ride or walk your dog together or go to an art museum. Make your own rules.
posted by judith at 8:14 PM on February 3, 2008

Avoid the pick-up artist crap, remember that you have two ears and one mouth, and don't take it seriously. Your town probably has a craigslist and don't try to meet someone you imagine in your head; the person you're meant for might be a total surprise and you won't know it until you give each other a chance. Just go and have fun (great places to date include bars, ice cream places, and anything that will give you something around to comment on ala "did you see that four year old scream for that second scoop? I thought I'd I have to tell him that you KANT always get what you want"). If there isn't a craigslist in your town, singles ads and other online services help.
posted by history is a weapon at 8:20 PM on February 3, 2008

Important question:

When you say you've never had a "date". Do you mean that you've never had sex? That you've never had a relationship? Or just that you've never gone through the particular courtship ritual that we call a "date"?
posted by TigerCrane at 8:20 PM on February 3, 2008

@sully75: If it's helpful, I would say that there are three main reasons I have not yet been on a date. Through high school and college, I was extremely involved in academics and did not have much of a social life in general. Also, I suffer from social anxiety disorder, and I have only begun receiving treatment within the last year. Finally, the few times I have tried to ask someone out, I have been turned down. A couple of those people have since become friends, but they have not felt romantically attracted to me at any point.
posted by philosophygeek at 8:25 PM on February 3, 2008

Lord, whatever you do please don't listen to yoyo_nyc. That's not even going to come close in approaching the level of quality of anything you want to end up having. In fact, it'll probably delay you from getting that.

Group date?
posted by twins named Lugubrious and Salubrious at 8:29 PM on February 3, 2008 [1 favorite]

@TigerCrane: All three. I have never had any romantic relationships nor done so much as hold hands with a girl on the physical side of things. While I have some female friends and have done normal friend-activities with them, I have not done any one-on-one events (nor multi-couple events) in which there was anything more than platonic interest.
posted by philosophygeek at 8:30 PM on February 3, 2008

The thing you can do here is trust that you have enough native intelligence and wisdom to know what is going on in front of you and to do the right thing.

Keep eye contact and smile. Be your funny self, don't try to be funny.

This stuff isn't easy for anyone. Even people who do it a lot still find it challenging, so there is nothing wrong in feeling nervous or not sure what to do. The fact is that nobody is sure what to do and enjoying it means more about accepting the hard parts and not fighting them.

I still haven't figured it out and for that, I'm glad.
posted by Ironmouth at 8:32 PM on February 3, 2008

Also the advice to ask about something specific is really good. I say something along the lines of "I would like to take you to dinner" or something like that. I make it as clear as I can what my intentions are. Let her know that you want to take her on a date.
posted by Ironmouth at 8:35 PM on February 3, 2008

I did not date until I was 29. The big revelation I learned from all this is that appearing desperate or needy, even in the slightest degree, is the root cause of most beginner problems. This forms Crapmatic's Axiom #1: Adopt a "don't give a crap" attitude in your personality, and work on fulfilling yourself without the need for someone else. Do things that make you happy and that elevate you on Maslow's hierarchy, do not settle for the same old routine every week, tackle things that impede your self esteem (lose weight, for example), and put the highest priority on the things that mingle you among people. You'll then have the charm and charisma to attract other women or the confidence to casually ask someone out for coffee where you can brush off a rejection with no second thought and move on.

Yeah, you could do the Guido methods but seeking easy lays would probably not net you the kind of quality women you'd be happy with in the long term. I'm skeptical of dating services, especially since they tend to be sausagefests; I tried them with poor results. I'm married now and my wife is someone I met in my career field.
posted by crapmatic at 8:48 PM on February 3, 2008 [2 favorites]

It's basically two people spending time to see if they might have romantic and/or sexual feelings for each other. There's no formal structure to the meeting. You get together, you greet each other, you do some sort of activity and try to interact. Like many other people have said, it's a lot like hanging out with a friend.

I didn't go out on a date until I was in my mid-twenties, either. There's a lot of good advice here. I'll add:

Make sure you go. Even if you come up with a million reasons not to go the day or hour before, and it turns out to be a terrible date, you'll feel very relieved that you have gone out on a date and will be a little less tense on future dates.

Also, don't get down on yourself if it's not great. You may be inexperienced, but there's lots of causes of bad dates, most having to do with incompatibility. The ratio of bad dates to good ones is extremely high for most people. Not expecting it to be great might help you be less nervous about it.

Good luck.
posted by ignignokt at 8:49 PM on February 3, 2008

I think specific is good, but it should be even more specific than going to dinner, more like alicetiara's suggestion of a particular event. The event should relate to something you talked about or find interesting.
posted by sweetkid at 8:52 PM on February 3, 2008

Learn to dance the ratio is incredible in those free dance lesson going around town it will get you over your shyness by you being the center of women attention. Also a guy who can dance for some strange reason is sexy to women. You seem like an active guy i would suggest instead of trying places like bars try to center around stuff you are interested in like maybe go down to a local campaign office and help out around there more women are prone to volunteer then men.
posted by Rolandkorn at 9:09 PM on February 3, 2008 [2 favorites]

The purpose of a date is to go out & have some fun with someone else.

Not that hard. Just remember the other person is a person too and has the same fears, hopes, and desires as you do.
posted by panamax at 9:12 PM on February 3, 2008

Specific is great. Nothing is worse than "i really like you," and then the big awkward pause as you put all the pressure on them to react. I know from experience.

Think of it as a date or just a fun evening out- nothing more, nothing less. Don't put too much pressure on it to be the beginning of some earth-shaking relationship. I think that's the main "mistake" people make. No matter how experienced you get, most dates don't turn into a relationship, for a hundred different reasons that you have no control over.

Also, the other person may not even know you're inexperienced. It took me a while to get started dating too, but I think I was able to "play off" my inexperience pretty successfully. And if the girl does know, so what? She's on a date with you because she likes you.
posted by drjimmy11 at 9:14 PM on February 3, 2008

what really helped me, and it took me until after the age of 30 to fully realize this, is that everyone has their "constituency" or audience. As a younger man, I thought there were certain guys in the world who were "good with girls," and I would never be one of them.

Because I grew up in a blue-collar, fairly closed-minded city (hi, Baltimore!!), I assumed all women were into jocks, or guys who drove nice cars, or who pretended to be gangsters, and that I would never be one of those guys- so I'd always be lonely.

I'm not saying everyone in Baltimore is like that, but I was hanging around people who just would never be into me, and thinking that was everyone in the world. After re-locating to a bigger city, i realize there are people who get off on smart, or geeky, or just about anything. Go find people who are into what you're into.

Example: There are a lot of girls who like to date musicians. They probably won't want to date you if you're not a musician.

Does this mean musicians get "all the girls?" No. they get all the girls who are into musicians. There are also girls who would be into you who wouldn't look twice at a musician/jock/whatever. You might not believe it, they might not be easy to find, but they are out there. Good luck finding them.
posted by drjimmy11 at 9:30 PM on February 3, 2008 [2 favorites]

Hire a prostitute.

Seriously. There is nothing less attractive than sexual desparation, and people can tell. I think they can smell it...its reasonable that there would be pheremones. You'll be much more sexually attractive if you actually HAVE sex.

Then there's the matter of having actual flight time when you DO score...how nervous do you think its going to make you to touch your first pair of boobs?

There's a phenomenon called "rapport" where people tend to experience the emotions that the people around them are experiencing. It makes you happy to be around happy people. It makes you nervous to be around nervous people. Fear and frustration are pain states, so people avoid people that broadcast them.

its important that you get a good one, however. The higher end prostitutes are accustomed to playing therapist. Go to The Erotic Review an find a girl in your area with good reviews. Pay around 300 bucks. Tell her it is your first time, don't fake it. She may be able to give you good technique tips that you can use with lovers.
posted by TigerCrane at 9:39 PM on February 3, 2008 [4 favorites]

I would recommend the pick-up-artist stuff. In fact, I'd recommend that you read everything that you can. How intellectually legit is it when people tell you NOT to educate yourself? You don't have to like Machiavelli, but if you are a professional statesman, you have to read him. if you find techniques that you consider unethical or uncomfortable, don't use it. (Although I'd ask yourself if the technique makes you uncomfortable because its a bad idea, or because it makes you step outside your comfort zone).

I'd also recommend the material at seduction.com. The mystery method may be hard for you to pull off, since it focuses on projecting the image of an sexually confident male, which may be tough for a 26 year old virgin. Speed seduction may be better suite to you. But you need to familiarize yourself with both.

Honestly, how could the "layguide" stuff NOT work? Any kind of focussed study, coupled with experimentation in the field is bound to work better than doing nothing at all.

As I said, read everything, but I would caution you to be careful with the mass market books that are written for men by women: Straight women do not know anything about pulling women.

I'd recommend you lose your fixation on "dating". Dating is for women you are already sleeping with. Dating implies a formal, uncomfortable, ritual. Don't date. Hang out with, spend time with, do things with, but don't date.
posted by TigerCrane at 9:39 PM on February 3, 2008 [1 favorite]

I've only browsed this site, but I think it might be helpful. The idea behind it is to make yourself comfortable with social interaction in general, which then leads to dating not seeming as scary. It's probably at least worth browsing to see if it strikes a chord with you.
posted by MsMolly at 9:44 PM on February 3, 2008

I'm particularly nervous about what to do on a date, especially given my absolute lack of experience.

Be funny. Don't drink too much. Smile a lot. Don't talk about your inexperience with women, just as a lothario shouldn't (you'd hope) talk about his extensive experience with women. Discuss your common interests. Don't try to impress her. Relax. Have fun. Don't drink too much. Your first few dates are probably going to be a little awkward no matter how you prepare. Learn from them. Don't drink too much.
posted by Optimus Chyme at 9:56 PM on February 3, 2008

I too was a late bloomer, and have also struggled with social anxiety, so I relate to your situation.

Results may vary, but I recommend using an internet personals site. I have found the one that links to nerve, salon, the onion, etc. to be full of interesting and intelligent women. The great thing about internet dating is that the premise is clear from the outset. You skip the step of moving from a random social encounter/platonic friendship to a date.

As for the date itself--in my book, the main attraction on a first date is conversation. Meeting for drinks/coffee is good. A little alcohol is a good social lubricant, just don't overdo it. I don't like dinner dates for first dates. I'm generally not relaxed enough to enjoy the meal, and this can be expensive. Dinner dates are for down the road. . . Museums are good. Parks are good. Movies not so much, because you aren't interacting.

As for your fears of coming across as naive. . . My advice is to cut yourself a lot of slack. You ARE naive--that is, you're just beginning to open up this new facet of your life. So you shouldn't expect yourself to be, or appear to be, experienced. This probably won't be much of an issue on a first date, though. As I said, mostly a first date is just conversation, getting-to-know-you stuff. This is fun and interesting, in and of itself. Just enjoy the conversation. Ask questions and be a good listener. Share your stories.

And expect to go on a lot of first dates before you make a good connection. I mean, you might get lucky, but generally it's a bit of a volume game. As I said, enjoy these dates. You can learn a lot from other peoples' experiences. Don't worry too much about sex and romance, right at first. Initially, you're looking for a woman you enjoy talking to and being around.

Because your lack of experience makes you anxious, you may find you have the impulse to bring it up in conversation. In my book, no topic is off-limits, even on a first date, but it isn't really necessary to go there, early on. Talk about other aspects of your life--your job, your studies, your interests and passions. If she asks you about your relationship history, it's totally fair game to just say "I've been single for a while." White lies are fair game, in this regard, at first. When you've gotten to know someone a little better, and feel comfortable, you can open up more about this. On the other hand, if you do feel comfortable, and the topic comes up, and you feel like it, go for it. Women will find your honesty attractive, and a great many will find your lack of experience attractive, in and of itself (they will want to be the woman who deflowers and corrupts you). In other words, you can't go wrong, so just go with what you feel.

Finally, standard first date protocol is to tell your date that you had a nice time, and that you'd like to see her again (if this is true--omit if not true, but still say you had a nice time). A kiss goodnight is standard. You might be most comfortable with a kiss on the cheek, but a light kiss on the lips is always acceptable, so go for it if you want to. (Depending on chemistry, there's really nothing off-limits, even on a first date. But even if there's major chemistry, you might be most comfortable if you pace yourself.)

It's past my bed time, so here endeth my treatise on the art of love. Good luck, and we'll be eager to hear how it goes. Come back for more advice as desired.
posted by flotson at 10:01 PM on February 3, 2008 [1 favorite]

2 ears, 1 mouth. Use them proportionally. This may be applicable to other body parts later, depending on how successful your date is.
posted by Inspector.Gadget at 10:11 PM on February 3, 2008 [1 favorite]

Also, don't take dating advice from Ross Jeffries, a dude who looks like this.
posted by Inspector.Gadget at 10:13 PM on February 3, 2008 [1 favorite]

I'm 22, straight and female, and I find I often date up a little in terms of age, because my age group is full of guys who still act like they're in high school, and they think girls are either too mysterious or just sex objects. Avoid either extreme; girls are your equals, act accordingly. Just make sure you aren't projecting weirdness of some sort; don't tell the girl she's pretty even if she is (other compliments like on clothes are okay), don't talk about your inexperience right away even though it's good to bring it up in a casual way after a few dates, and try to talk about the same stuff you talk about with friends. Humor is great when done naturally and not in a cheesy way. Chances are you will still give off the weird signals and some girls will run, but it will be so subtle that you won't even realize it until later. Then you'll have some dates where you do everything right, but you're still not a match, and you'll feel weird because you don't know how to talk to the person in a way that clicks just because you're too different. So go on dates, expect to screw up and not end up in a relationship right away, and try to enjoy yourself anyway.
posted by slow graffiti at 11:08 PM on February 3, 2008

This might not be the advice you're looking for but I strongly suggest The Internet to help you overcome your anxiety and getting to know someone before you go on The First Date. I've always found it much more easy to open up online than in person and you don't have the stress of appearances (oh god do I have food stuck in my teeth?!) to worry about. I don't even necessarily mean dating sites, but rather forums or communities online that are in your area of interest. That way you know you already have things to talk about if you end up going on your date.

I have quiet a few friends in their early 20's who haven't been on much more than a first date, let alone any sexual experience. They're all sweet, decent guys who seemed to always fall into the "friend trap" whenever a potential girlfriend came along. I'm not a fan of all that pick-up artist techniques but reading about it can also help you decide on what you SHOULDN'T be doing.

I may be alone in this suggestion but definitely be honest. I don't mean pour out the truth about your lack of past experience upon first meeting but don't do the opposite and pretend to be someone you're not either. Personally, I find it kind of sweet and endearing and hopefully you'll find yourself on a date soon.

I suggest the interwebs as an option because I'm bias. I met my lovable, weird, just-as-insecure-as-me guy online and I couldn't dream of a better companion in life.
posted by liquorice at 11:49 PM on February 3, 2008

Regarding having a specific plan/suggestion, get in the habit of doing things that are date-friendly. This means that because of your hobbies and interests, you constantly have activities coming up that could be dates, but which you would be doing anyway.

Because you would be doing them anyway, you're not needy when asking if someone wants to join you or come along, and so the pressure is off, meaning you will make a better impression.

In your case, you might want to also make it clear that you're thinking "date", rather than offering friendship. "Hey, I'm doing X next week, I was wondering if you'd like come too - sort of a date thing?", because it would suck for the two of you to be on different pages on that aspect, which may be a risk in absence of immediate chemistry.

Expect some rejections. It might help you feel better if you have a rejection response at hand, so you can handle it suavely, instead of feeling like you made yourself look foolish, which can eat at your confidence for next time.
"Well, I guess I'll just have to endure having all the X to myself!"

Lastly, don't listen to me :-)
posted by -harlequin- at 1:43 AM on February 4, 2008

ow can I get over my fears of coming across as romantically/sexually naive?

Allow it to be an endearing quality, rather than a lack of qualification.
For some people, innocence is a turn off, for others, it's clay waiting to be shaped...

Also, don't listen to me :-)
posted by -harlequin- at 1:46 AM on February 4, 2008 [1 favorite]

The pick up artist stuff *can* be helpful, I think, in very specific ways. Being confident, expecting some rejection, learning to deal with that... those are all good things. But they take that and work towards a goal of sleeping with a lot of women, which is very different to dating women and finding someone you like.

I haven't been on many dates in my life, but I was brought up around lots of women so I can manage to either be comfortable or fake it when I'm with someone new. I'd feel very awkward at something as formal as dinner. I just started seeing someone new and the date was coffee and a crossword. Very low key, very casual, but it let both of us know enough about the other to know we'd like to do it again.
posted by twirlypen at 2:13 AM on February 4, 2008

I second, third, fourth or whatever the pick up stuff also. While some of it is totally geared toward getting sex. A lot of it is also self-help oriented and geared more toward getting a girl then leaving the rest of the choices to you. I really like David DeAngelo and I think he is perfect for you. He focuses a lot more on dating and how to get the girl, rather than being some sort of player. Though if that's your goal go for it.

I've never had any problem having dates, but have had problems in other areas. I've always been involved in various activities with other people and have had decent groups of friends. Just being myself, being involved and around others has always seemed to bring girls around.

Some important points for both getting a date and being on a date are... Making sure to take care of yourself. Look nice, work on losing weight if you have excess, shower, haircut etc. Be funny and flirtatious. Talk about your passions in life, but make sure to not go overboard if this is something that your date is totally not interested in. Be confident (I know this can be hard). Be the leader of the date, have a plan. There are tons of others. And I don't know where your starting from and what you need to work on.

And while the other posters idea to get a prostitute might sound like a real bad idea, it's true that a girl will instantly know about your lack of sexual confidence and until you gain some, you're not going to be able to get the girl you deserve.

While I understand you have no experience in this area, you may even be in a worse situation of lacking normal social skills (which I'm guessing you do to some degree, because of the social anxiety disorder). You might want to really work on this either at the same time or in congruence with the dating, because this plays a hugely important role. Once again back to the seduction stuff. If your in a major city (maybe even smaller places) you can find groups of guys working on their dating/pickup skills. I would recommend joining these guys, a lot of them come from similar backgrounds as yourself and have totally flipped themselves around to become great at it. It's going to require a lot of work and a lot of tough times, but if you really want to fix this and end up with the woman you deserve I would recommend it.
posted by bindasj at 3:08 AM on February 4, 2008

Dude, I think you sound like everyone else on this site. Social anxiety is the new flu. My guess is you'll be fine in the long run.

It's weird because I don't consider myself sexually attractive but a few women have. My confidence issues have fucked things up for me way more. I'm working on that.

I read this recently...it was interesting. Flirting kind of goes with dating. Think of it as playing.
http://www.sirc.org/publik/flirt.html

Like I said earlier...just prepared to get some knocks. It's like playing the violin, you don't get comfortable with it right away. You have some catch up to do, but I bet you'll be fine.

Try okcupid.com. Seems to be filled with like minded people.
posted by sully75 at 4:35 AM on February 4, 2008 [2 favorites]

Oh yeah, dance classes are awesomely awesome. You can be physical around real life women. It's pretty sweet.

I recomend Argentine Tango classes. Make sure they are into beginners.
posted by sully75 at 4:36 AM on February 4, 2008 [1 favorite]

Always call back for another date. Even if you don't think you hit it off. Wait a couple of days, then do it. Every girl.
posted by Laugh_track at 6:21 AM on February 4, 2008

I've watched a few episodes of The Pick Up artist show guy or whatever it's called on VH1. I have to say, it does work for Mystery and his two wingmen. But it works on a certain type of girl if you are a certain type of guy.

If you want to be a guy that just hooks up with girls at this point in your life, then yeah, you should probably go with his advice. Go to bars or places where girls go to play the mating game, insult them or do whatever he does, hook up because those girls think you insulting them is a sign of your confidence. Win!

But if you want to go on a date and have a meaningful relationship... it's something you learn through experience. Don't be yourself, laugh at the wrong moments, snort, talk about yourself too much - most of us have done it. And hopefully, most of us have learned from it. You just have to take the first step!
posted by spec80 at 6:53 AM on February 4, 2008

Re: Prostitute stuff. If you're looking for a relationship, not necessary. Girls that are really into you will work with you on your lack of sexual experience and will not dump you because of clumsy or nervous performance.
posted by ignignokt at 7:47 AM on February 4, 2008 [2 favorites]

As a late starter, it can be hard to focus on the fact that you are not just on Your First Date, you are on Your First Date With X. Don't allow yourself to dwell on the former, it'll show and it's very off-putting for a woman to feel that you would be just as happy to be out with any other girl because the main thing is that You're Finally On A Date.

In terms of the date itself, I think you can define it as a success if she has a good time, whether or not she wants to see you again. The basic rules are to have a plan, and to have thought about things enough that you can provide specific options "Do you want to do X? OK, how about Y or Z" instead of asking "What do you want to do?" This serves your main goal of showing her a good time. It's great if she has suggestions, but don't give her the burden of thinking of something to do.
posted by teleskiving at 8:07 AM on February 4, 2008

Why do you need to "date"? Go out and hang out with people you like in groups. If there's anyone you click with, see if they want to go have coffee or watch a movie sometime. It's more "natural progression" than "date."

I'm a 29yo straight female parent on her second marriage, and I can count the number of actual dates I've had on one hand (and they were all in the context of a romantic attachment that already existed, except when my now-husband and I went to Team America: World Police together--that was planned as a group outing until we found out no one else wanted to go, but it ended up as a "real date").
posted by Cricket at 8:18 AM on February 4, 2008

I have two pieces of advice for you.

One, embrace the fact that you are "a 26-year old straight male [who] for a variety of reasons [has] never been on a date."

By which I mean, no matter what materials you consume about how to act going forward, don't engage in any kind of behavior that involves pretending you're anyone other than you are. If you have an awkward moment, be calm and say, gosh, sorry, I just don't have a lot of experience with this. You don't need to belabor the point up front that you've had a different history than most other people but you are who you are and your goal is to meet and know people who like you for the person you are and the person you're trying to be.

Anyone who makes you feel like shit about this is someone you don't want to know anyway.

Two, be prepared for the fact that interpersonal relationships, conversations, getting to know people, dating, etc ad infinitum are all acquired skills.

Which goes back to point one, meaning just accept that this is nothing more than a subject you don't yet have a lot of knowledge and skill with, nothing more. You'll have to try and practice before you get better. Sometimes that's hard work, like lifting weights or learning a new language, and you just have to slog through it. It wasn't until my middle twenties before I decided that I had no excuse for not knowing how to strike up conversations with strangers at parties and other gatherings and I needed to figure it out.

And holy hell but did I ever suck at it at first. But I got somewhat better.

Who knows, maybe you're nothing like me and I'm just projecting. But I was someone who followed the nerdier path in life through high school and a lot of life. I found that when I started to want to change those aspects of my existence that the biggest impediment I faced was myself: feeling shame that I didn't know the things that other people seemed to do easily and instinctively, and letting that shame and fear keep me from doing it. I knew, but didn't really understand, that the reason they did that so easily was that they'd just practiced and made their mistakes earlier in life.

So I guess my answer to how you get over the fear is that you don't - you just do it anyway. You didn't really get over the fear when you were engaging in those academic pursuits - we're all afraid when we start something new. But we accept that we address the fear of competence by becoming competent, which we do through study and effort.
posted by phearlez at 8:49 AM on February 4, 2008 [5 favorites]

I would suggest reading the pickup stuff, but be careful because there are a lot of misogynistic undertones (and overtones) to all of it. A lot of the guys there are there because they are bitter towards women. However, there are people in those forums and sites that are genuinely interested in helping other people and aren't out to objectify or mistreat women.

Those sites can be a excellent source of information about confidence, dealing with rejection, and becoming a more interesting person. It might even be worth reading through the stuff because it kind of forces you to realize that there are a LOT of people out there who struggle with their personal lives more than you do.

With that said, there's a lot of trash on those sites. But you can get a lot of perspective from them too.
posted by PFL at 9:35 AM on February 4, 2008 [1 favorite]

how can I get over my fears of coming across as romantically/sexually naive?

The only way you will "get over" these fears is to go on dates. In the beginning you are going to be stuck with these fears, this nervousness. Explore these fears. Get to know them. Go on your first date despite them. Later on this will be replaced with new fears about how the particular woman you are going out with feels about you.

Do talk to women. Don't run around giving her your number. Get her number, call her in two to four days, and ask her out.
posted by yohko at 10:26 AM on February 4, 2008

Ok, this is more in addition to a fair amount of decent advice you've been given upthread (and, generally, listen to the women more than the men—they're telling you how they like to be picked up).

First off, since you weren't dating, you must have been doing something else, right? You're probably really good at something else, right? Philosophy, maybe?

So first off, you'll probably find it helpful to look in pools where there's a shared interest. There are plenty of girls who are into philosophy and, if my experience in college philosophy classes is indicative, they're not necessarily doing a lot of dating either. I dig the smart girls, though, so that might be different for you.

You progress to a date either from knowing someone and asking them out, or by going blind (usually through the internet), but in either way, you can come up with something that you'd want to do anyway. I tend to believe this is key, because while you want to be interested in the girl and you want her to enjoy doing whatever it is you've decided on, dates really suck if you're not so into whatever you're doing (as an advanced step, don't be afraid to bail on regular plans if things start to suck). So, you've got something you're interested in, so you invite her along. Then you go and do it together. If it doesn't work out, well, no harm no foul—a single date is not a life commitment.

That's how you get dates. Moving to consummation? Well, I have to say that I still don't understand that one so well myself, except to say that flirtatious touching helps and that likely the girl you're out with will have some idea on how to move things forward. Women who expect you to lead every interaction are kinda a pain in the ass in the long run anyway, so there's no shame in having things not work out.
posted by klangklangston at 11:17 AM on February 4, 2008

Nth dancing lessons... seem to be always a need for guys and you get to rotate through the girls, and you're both clumsy retards who step on each others feet. Forget pick-up stuff, girls that fall for that are girls you don't want anyway.
posted by zengargoyle at 11:21 AM on February 4, 2008

On prostitutes and pick-up-artistry: it's probably a good idea not to use any technique for gaining experience that, four years down the line when you're engaged, you'd be embarrassed to tell your fiancee about. Naivete is understandable and sometimes even endearing, sleaziness much less so.

You know how you're supposed to go on job interviews for positions you're not crazy about, because even if the opportunity sucks, you get interviewing experience? Dating is a lot like that. Even if you go on a date with a stick in the mud or someone who picks their nose at the table, you learn a bit more about what to expect and what you want. And, really, it's not a bad idea to go on a few dates you're unenthusiastic about to get those experiences under your belt. Going on a date is somewhere between going on a job interview and hanging out with a friend - hopefully feeling more like the latter than the former. (Chivalry and romance and studliness are not as important as you might suspect. Women aren't expecting you to drive up in your Batmobile cradling a dozen roses and a Tiffany box in your mighty bicep.)

Also, keep in mind that, a lot of the time, she is just as nervous as you are. You're evaluating her, she's evaluating you, but your evaluations are not the final judgment on your dateability - just one relative stranger's opinion. If they don't think you're great, no problem. Someone will.
posted by Metroid Baby at 2:48 PM on February 4, 2008 [2 favorites]

I would suggest reading the pickup stuff, but be careful because there are a lot of misogynistic undertones (and overtones) to all of it.

No, no, no. Just skip it. That shit is for men who don't like women. I don't know what their problem is, but it's sad and pathetic and retarded, and the kind of men that stuff works for, and the kind of women that stuff works on, are sad and pathetic and retarded.
posted by Optimus Chyme at 5:00 PM on February 4, 2008 [1 favorite]

Yeah, I'll go ahead and second that from Optimus. There's an old joke about a guy who figures out that a dog turd is the secret bait for catching fish, and it ends with the line "Yeah, but they taste like shit." Even if the supah-fast seduction techniques work, everything they catch tastes like shit.
posted by klangklangston at 5:45 PM on February 4, 2008 [2 favorites]

As sexually desperate as you are, you're going to find some girl to ask out, so I'll skip to the next step- the date itself. My advice is, don't go on a "dinner date". Or any other type of date where you are essentially interviewing the other person face-to-face. For someone with social anxiety, and a first date scenario, that's a disaster waiting to happen. Try walking through the park. You'll pleasantly find there are no awkward silences. Concentrate on your goal- namely, getting through the date without making a total ass of yourself. Don't try to show how clever you are, because you're gonna screw it up- at least on your first date. Quite possibly I'm just talking to myself here. Anyway, good luck!
posted by proj08 at 6:15 PM on February 4, 2008

Adding to the fray.

I would never, ever recommend someone in your situation to start by looking at the words of wisdom of the so-called "seduction community." Whatever their merits, sites like Doubleyourdating, Speedseduction, etc. aren't designed for someone who's just beginning to work on improving their social skills. Don't believe me? Check out A Long List Of Ways The Seduction Community Can Make You Weird.

Here's the good news. You're willing to change, and you're willing to work on yourself. I can't recommend SucceedSocially.com higher. It's honest without being condescending, and gives very clear, very helpful advice that's focussed on personal growth, not just finding women to have sex with you. The bottom line? The more you work on making yourself awesome, the more likely you are to find awesome people. Awesome women will number among them.

Good luck.
posted by awenner at 9:21 PM on February 4, 2008

Thank you for the suggestions thus far; they have been quite helpful. I still have some questions about the specifics of a date. How long should a first date run? One poster above stated that a kiss at the end of the night is standard; is that a consensus view? Finally, are they any things that are obvious to you now but came as a surprise when you began dating? In other words, are there things I should have learned from dating experience that women will be expecting?
posted by philosophygeek at 8:06 PM on February 5, 2008

The standard drill:

First date is coffee or drinks. There was a study done that showed that women prefer coffee on a first date (presumably due to the fear that they will get drunk and do something stupid) and men prefer drinks (presumably due to the hope that the women will get drunk and do something stupid). The idea is to keep it casual and short, so there is no awkwardness if it oesn't work out. Its easy if you're having coffeee to announce that you have somewhere else to go, plus there is the option to extend it if it IS going well..."hey, are you hungry? Want to grab some dinner" The initial coffee date can be skipped if you already know each other pretty well.

Second date is more elaborate. A nice dinner is traditional, but I don't recommend it. Gallery Openings, roller skating, comedy club, something fun that you can do together. Usually there's a kiss at the end of the night. But if there is no kiss, you haven't NECESSARILY been rejected.

Third date is sex.

that's the traditional dating format. In real life it can go very differently.
posted by TigerCrane at 10:11 PM on February 6, 2008 [1 favorite]

I think it should run long enough that you get a chance to relax, show yourself a little bit, get to know how the person feels to be around. There is a point where it will become taxing and weird to be with a stranger and I think you should break it off about 10 minutes before that happens. Unless you have stars in your eyes and everything is amazing.

If it's a blind/internet date, I would probably recomend planning on not kissing the person on the first date. Again, unless things have gone really amazing. Don't add to your stress.

I've been on a lot of dates, it's still confusing. Try to be positive about your life and yourself. That's my fatal flaw.
posted by sully75 at 4:03 PM on February 7, 2008

Philogeek—The first date is traditionally for awkward fumblings. The second date is traditionally for more assured fumblings. By the third date, you should know whether you're likely to have sex or not. But the real problem with this is that the fumblings are almost always fraught and nervous even for experienced daters, and especially if they really like someone. So the best advice is really to give the date a try and just have fun. I've found that being honest helps, like saying "I'd like to kiss you" before you do. For other people, or other girls, that comes across as awkward or needy or whatever, but hey, I don't date those girls.
posted by klangklangston at 4:21 PM on February 7, 2008

A kiss on the lips is NOT acceptable to everyone in the first date.
posted by KB.Boston_implant.By way of NY at 8:22 PM on February 9, 2008

Get used to the idea, its unlikely to go "right" the first number of times you try it.
posted by browolf at 4:57 AM on February 17, 2008

Dude I'm 28, and I also never dated. But I decided to work hard to do it.

Why I didn't date?,

a)in my teens because i had a low self esteem, and only played video games and play lots of men sports (I'm straight).

b)In my early 20s I become a scientist wanna-be, only involved with books and studies. I really was into it, just because I was afraid to experience other stuff for which I was afraid to fail. I was a coward.

c) So I went straight to a PhD, where I decided to become more social, I did sports, went to parties, for some reason (I'm not ugly, and I'm in shape cause I clean myself properly and do lots of sports) the ladies got close to me. But, I started to suffering anxiety, and panic attacks (related to stress at work), so I went again into the "oh I'm afraid that this will make me fail in front of a woman", "I need to solve my problems first".

d) So I went to the psychologist, it helped me, but my studies begin to fail (for those of you in graduate school, you know that sometimes it can be stressing and time consuming, so if you lose lots of time, it takes lots of time to come back). But I decided to organize myself better, and start hanging out with friends again (fuck the PhD I've lost time by only being in that strange world called academia, were you find crazy people, loners, geeks, divorced people, stressed people, etc).

e) I'm not unsocial, but certainly have problems with intimacy, I left home at 17 so I'm not Mommy's son, I know how to be self-sustainable, but I certainly lack of experience with the opposite sex, although I have good female friends, but I haven't confessed to them my problem (although I think, at this time every one suspects, that either I'm gay cause all those chances lost, or a nerd).

So dude, START WORKING ON THAT NOW, we are smart people, we can learn things quick, but in relationships experience is everything. I don't wanna reach my 30s and still single, but I don't know if there are woman out there willing to give a chance to an unexperienced man.

I wanna know how many of you guys started dating late, and if there are women out there willing to love someone unexperienced, confident in some of his skills, funny, sexy, career-driven, knows to cook, to clean, to be responsible, but again, lack of the experience to be more intimate.

It is good that you started thinking about this, I spend 2 weeks of my vacations sorrouned by nature asking myself what I really wanted in my future. I found out that being on my comfort zone (science, books, academia) for too long was an immature and selfish way to live. We have to share happiness and love with people, friends, family. True happiness is only achieve by sharing it.

Good luck. And let us know if it worked out.
posted by gradstu1980 at 4:49 PM on February 28, 2008 [1 favorite]

Seconding the request to let us know how it works out. We're rooting for you!
posted by jtron at 5:13 PM on March 5, 2008

So far, the update isn't too encouraging, although I now have a better guess of why things aren't working. The followup question is here, and I'm open to whatever suggestions others may have.
posted by philosophygeek at 6:30 PM on March 5, 2008