How to ask women out without seeming creepy or desperate
May 11, 2016 1:47 PM   Subscribe

I am single after an 8 year relationship. I was engaged. I have no idea how to navigate today's dating landscape. Most of my past relationships have developed out of having regular contact with someone for a long time and getting to know them and become friends. Details inside....

I broke up with my fiance' (we were together for 8 years). It has been 9 months since the breakup. I still miss her but am lonely and ready to start seeing people.

I am worried that I won't meet anyone. Part of this is my anxiety/OCD talking. My last girl was gorgeous (out of my league looks wise) and we were into all the same stuff. I am a very specific type of person. What I mean by that is that I am into "higher brow" stuff, so I feel hamstrung that I am not into universally loved things like sports etc that would make me "compatible" with a larger number of people.

I look at online dating and don't see many people interested in the same things that I am (art films, philosophy etc). Everyone seems to be into the Walking Dead and sports.

I recently have had two encounters that gave me some hope but I am unsure about how to handle them without seeming creepy or desperate.

ONE - a girl in a wine store. I see her every week. She had a book that we stared chatting about last time.

TWO - a girl in a coffee bar (far from my house) that I was at a meetup (bookclub). Earlier in the day I was wearing a shirt from an obscure band. She was planning the pandora of that band. I said to her before leaving "hey, was that a "band name" pandora? I was wearing a shirt earlier today" Sure you were buddy was her internal response I'm sure.

The other thing is that I have no idea how old these women/girls are. I am 37 but look 25. I am not good looking (but in great shape) but super smart and witty (although I get nervous and it's hard to impart in a small interaction)

How do you ask these women out? It is so hard when just seeing someone somewhere.

Thanks in advance
posted by kbbbo to Human Relations (51 answers total) 13 users marked this as a favorite
A small tidbit; wanting a match to share interests with you is not the same as being snobbish about your superior tastes. The former is quite reasonable, but the latter is not and furthermore your bad attitude will be apparent and push away some women who *do* have things in common with you. Someone can like trashy TV and also be really sharp and be able to talk to you about books.
posted by hollyholly at 1:51 PM on May 11, 2016 [41 favorites]

seconding hollyholly. Also, you don't NEED to have so many shared interests; what's most important is shared values, not just interests. Try to be more easy going with your interests as the WORST thing is someone who is high strung about their likes and dislikes and doesn't enjoy things out of their comfort zone once in a while. I mean I'm all for a super fancy French dinner but does that mean I won't enjoy a greasy spoon once in a while?

Join clubs / try new hobbies that you may not realize you enjoy (I've had a LOT of luck with improv drop ins). Meet new people, make new friends first. Asking random girls out who are strangers isn't going to be as successful and making new friends and meeting potentials through there.
posted by rhythm_queen at 1:55 PM on May 11, 2016 [11 favorites]

I don't usually reply to my own threads but I do want to make a point.

I am not judging anyone for not being into what I'm into. Let me be clear about that. I just would like to be able to find someone that enjoys the ART that I do. It is a HUGE part of my life
posted by kbbbo at 1:56 PM on May 11, 2016 [2 favorites]

I look at online dating and don't see many people interested in the same things that I am (art films, philosophy etc).

Many, many women are into art films and philosophy. Have you tried going to museum meet-ups, or looking for these key words specifically on dating websites?
posted by roomthreeseventeen at 1:57 PM on May 11, 2016 [8 favorites]

I see you say you've tried online dating. Have you really gotten into the questions on, say, okcupid? Answering a ton of questions should help you find more compatible matches. That is how my boyfriend and I met, and I do not like sports. Neither does he. In fact, I went on dates with many men who did not care about sports there. So, you might want to try to really invest in an online dating profile before you decide it's not for you.

For women you see out and about, you can do what you did at the wine store, and bring up a common interest that you know you share. Like a book, or a band. If you start having a good conversation, you can then just ask her out. Say something like, "Hey, it'd be great to continue this conversation over coffee sometime. Are you free this weekend?" She might say no, but you have to try in order to have a hope of going on a date. However, as a general rule, I would never give my number to a guy that I met just out and about. That may just be me, but I think you will have a lot more success dating online. Online, you know that the people are interested in dating. In the real world, you have no idea, and especially if they are at work somewhere, that can make the interaction very uncomfortable for them. So you may want to think pretty carefully about who you asked out in person. Don't ask out people who are working.

Also, as an aside, there's no reason to call women "girls."
posted by sockermom at 1:59 PM on May 11, 2016 [39 favorites]

Please, please, please don't ask women out who are employees of a store you are patronizing (regularly or not) unless you're so sure they will say yes that it is practically a formality.
posted by griphus at 1:59 PM on May 11, 2016 [44 favorites]

1. You're 37. You should not be dating girls, period! Getting into the mindset that these are fully developed adult human individuals with their own independent stuff going on will help you not be creepy in your interactions with them!
2. Asking strangers out on dates in neutral locations like stores and coffee shops is just creepy, full stop, sorry. Women just want to go about their daily lives. It is fine to chat with people, and if you work up a rapport over time (i.e. you're no longer strangers!), maybe ask about grabbing a cup of coffee -- but approach this as general life friendliness, not as a dating strategy. If you want to try picking up strangers, go to a bar where that's the vibe. If not, I would work on expanding your social circle generally, and/or online dating.
3. I would try to chill out on the high brow/low brow stuff. Just because someone has Walking Dead on their profile does not mean you need to watch Walking Dead with them or that they aren't capable of "high brow" conversations. I have a PhD and can high brow it with the best of them, and I still watch some pretty trashy TV (waaaaay trashier than Walking Dead, believe me!)
posted by rainbowbrite at 2:01 PM on May 11, 2016 [63 favorites]

rainbowbrite has a really good point as well. My husband and I go to MoMA or the Met almost every weekend, and I spend a lot of time watching Survivor, while he likes to watch 50s cult horror movies. You will miss out on great people if you box yourself into one type of person.
posted by roomthreeseventeen at 2:04 PM on May 11, 2016 [10 favorites]

Also, I totally get where you're coming from wanting to share common interests. But it actually really is more important to share respect and interest in the other person. For example, my boyfriend is really into a few science fiction fantasy worlds that quite frankly I do not really grok. But some of our best conversations are when he describes these things to me. He shares them with me, I listen, and it's really fun to see how engaged he is in these topics. I don't know much about them, and I wouldn't pursue them on my own, but learning about them from him is a really fun experience. What matters is not sharing an interest, but respecting your partner's interests.

So, it is totally fine if you only want to date people who like the art that you like, but you also will need to recognize that this is going to significantly narrow your dating pool.

So, it may be worthwhile going on some dates with people who seem cool and fun and who don't necessarily mention your specific interest in their dating profiles, assuming you're dating online. Who knows what will happen? Narrowing your options significantly at the get-go may shut out some really great women.
posted by sockermom at 2:07 PM on May 11, 2016 [1 favorite]

Consider age-appropriateness. You don't mention the age of these women you've been eyeing but,given their jobs, they're likely to be younger, maybe in their twenties. You're 37. It's not illegal to date recent college grads, but it's a lot easier to cross over the line into creepiness with them.

The good/bad thing about online dating sites is that virtually everyone there is actually looking to go on dates. So it's generally entirely appropriate to ask a person out after only a few reasonably-successful conversations. That's the point, they've signed up for that. It makes that transition much less awkward. Of course, it also means that any given date is less meaningful/fraught than if you were asking out the cute woman in your Greek art appreciation class who you've been chatting with for months. But that's the tradeoff, and in terms of building confidence, it can be very helpful to have a few invitations in a row accepted. (Tip: if your "willing to date" age range on the site does not include your own age, you're being a creeper.)
posted by praemunire at 2:09 PM on May 11, 2016 [19 favorites]

To address your concern about meeting people, I wonder where you live. If you can get to a city, I think you will see many many women online who are into art films over sports.
posted by kapers at 2:14 PM on May 11, 2016 [1 favorite]

Your unnecessary comment about your ex being gorgeous makes me wonder if you're preoccupied with finding another certified Gorgeous® person in addition to all your other requirements. I'm not trying to be judgmental about your preferences for looks but I'd suggest keeping an open mind and try to talk to and get to know a woman before writing her off as "not hot enough".
posted by a strong female character at 2:23 PM on May 11, 2016 [27 favorites]

Please, on the grave of Deleuze, stop spending so much energy judging your own attractiveness and what "specific type of person" you are. Did you do that before you dated your ex?
posted by rhizome at 2:29 PM on May 11, 2016 [13 favorites]

First things first. You're not looking for a large quantity of people. You're looking for someone who is compatible with you. So it doesn't matter if you're into art films and only 10 other women in your town like art films, or if you're into football and 1000 other women in your town like football. You only need one. Don't frame this as a numbers game, especially where personal compatibility is concerned.

That said, my partner and I share a lot of the same interests (and definitely connected on that front very early on), but we also have a lot of very incompatible interests that, on a dating site, would make us seem like a bad match (he likes pro wrestling! how did I even find this guy?!). It's probably not valuable to think of people as a reflection of their taste, or to assume that because someone likes sports or The Walking Dead, therefore you will not be compatible. You should be able to go have a drink and have something to talk about, but you don't need to be the same person.

But, OK. How to ask women out.

1. It should be a woman you have met and talked to/hung out with before. You have almost zero chance of getting a date from a first time casual meeting in a public place like a store or coffee shop. One of the reasons online dating can be nice is that you get to skip this step. But with in-person dating, it's vital. Honestly, it's not so much because asking a woman out in this way is "creepy". It's because I have nothing to go on. I don't know if we have anything to talk about. I have no context for who you are. Are you a serial killer? Do you hate my favorite movie? No idea.

2. "Do you want to go out on a date with me sometime?", alternately, "I'd like to take you out on a date sometime."

2a. If that really doesn't sound right to you, or is at way too high a level of difficulty: "I'd love to buy you a drink," "Would you like to go to dinner next Friday?", etc. As long as the proposed hangout is in a context which is culturally understood to be a date, you're fine. Just don't propose something neutral like coffee (friends go out for coffee all the time!), a museum, mini-golf, a hike, etc. If you don't say "date", you have to invite her to a cookie cutter stereotypical date or it doesn't count. My partner had a lot of trouble asking me out initially, until he used the magic words "dinner and a movie". Then I FINALLY got it, and it was a date, and everything went perfectly.

3. Go on the date. Smell nice. Be open and kind and have fun. Laugh at her jokes. Make eye contact. YOU WIN.
posted by Sara C. at 2:30 PM on May 11, 2016 [7 favorites]

I feel hamstrung that I am not into universally loved things like sports etc

Well, you don't want to date the whole universe, do you? You just need to find one that you like.

Art museums are great because the thing you like to talk about is right there. Even better are local art shows. You will meet people in the community and see some brand new stuff and people tend to be enthusiastic because it is locally and community driven.
posted by chainsofreedom at 2:32 PM on May 11, 2016 [3 favorites]

Most of my past relationships have developed out of having regular contact with someone for a long time and getting to know them and become friends.

So, if that worked for you, then, just keep doing that. Try to find ways to meet more people socially rather than trying to figure out how to ask strangers for a date. Go to meetups. Get involved in hobby groups. Go get involved more with the art scene or whatever it is that you are hoping a romantic interest will have in common with you.

(I have a similar history, fwiw. So this is a thing I have thought about and I have concluded that increasing my social exposure is the key.)
posted by Michele in California at 2:32 PM on May 11, 2016 [3 favorites]

Several observations:

1. You probably don't look as 25 as you think - take it from one younger-looking Old to another. People may sometimes mistake you for 25 in a dim light, and people probably think, due to your demeanor, clothes and partly due to your appearance, that you are somewhat younger than you are. This does not mean that you seem 25 on extended acquaintance, or that you fit in really well with 25-year-olds, or that you really, truly look 25. It is very, very easy to kid yourself on this issue - take it from one who knows.

Artsy amateur-academic men who date much younger women tend to end up rather unhappy at midlife, IME - the women get younger, the relationships get shorter and based more on "I will be briefly flattered by attention from this cool-seeming older dude" than on's something I have observed in contemporaries as I've gotten older. Seek out someone closer to your own age unless there is some surprise factor. Don't seek 25-year-olds thinking that you'll just troll around until you meet the right one; seek women your own age and only date younger if something odd happens on its own.

2. Honestly, normally hitting on staff (at the wine store or elsewhere) is creepy. But if you genuinely hit it off over a particular book, I think that's different. (I found a housemate that way! He is still with me, seven years later.)

3. I feel like you're mixing up two things to bad effect. You can either basically go on dates cold, as via OK Cupid, or you can get to know people. You can't get dates by being like "I also like this band, random girl I've met once!" Talk to this girl at bookgroup a few times, see if you hit it off, go to coffee.

4. Women are discouraged from seeming brainy because it puts men off. Bear this in mind. I - AFAB, no less - took until actually in my thirties to realize that plenty of women who didn't seem to care much about art films, philosophy, etc, actually were interested in those things but didn't make a big deal out of it, and what is more, had intelligent things to say. It is probably easier to find someone who likes the Walking Dead, sports and Agamben (or whatever) than it is to find your female opposite number. Women learn early on that acting like brainy men act is a sure recipe for rejection and shaming, so the few men who do want women who act like that are usually out of luck.

I'm assuming the "my girlfriend was so hot, another one like that pls" thing was an artifact of your writing, so let's leave it there. We all date someone irrationally hot at one point or another, and it's a one-off unless we ourselves are unusually hot.
posted by Frowner at 2:34 PM on May 11, 2016 [55 favorites]

So many great points above (judgment, attractiveness, "girls" vs. women). As for your specific question, "how to ask women out without seeming creepy or desperate?"

Without seeming creepy: Respect boundaries. Don't be a creeper, e.g. don't lurk and watch and wait for something to happen. If someone declines or shows disinterest, back off immediately and don't try again.

Without seeming desperate: Don't be desperate. Have a life outside of dating. Look at dating as just one facet of a rich, enjoyable, productive life that you lead. Once you meet someone you like, don't get overinvested and don't move too fast. Communicate clearly the whole way through and don't be coy.
posted by witchen at 2:35 PM on May 11, 2016 [3 favorites]

I forgot about the "how to" part of my answer!

So, go to a gallery opening with local artists. They are everywhere; it doesn't matter if you don't live in a big city - EVERYPLACE has a local artists' scene. Go and enjoy art. Chat with everyone there who seems receptive, regardless of age or gender. Then go home.

Surprised? Yes, you should NOT pick up anyone right away. You should instead concentrate on having a good time at this art show. Trust me, NO ONE is interested in the person who only attends events because they want to pick someone up. It's obvious and desperate, and nothing is less sexy. I know, I have been this person!

After you participate in a few local art events you will have a good idea of who is who in the community and who you like to talk to about art. Approach the person you like to talk to the most at the next gallery opening and ask her to go get a coffee with you.
posted by chainsofreedom at 2:39 PM on May 11, 2016 [8 favorites]

Approaching women in public works on TV but in real life it goes nowhere 99.9% of the time. This has nothing to do with you, it's just that most people in public are there to get something done, not to chat idly with strangers. (Notable exception: bars. People do sit around idly waiting for strangers to talk to them at bars.)

So if you do decide to talk to one of these women, ideally you don't go in to ask them out, just be friendly and let things go from there. If you get a strong response, like "oh my God, I love [band]!" and you have a longer conversation, then sure, you might ask her out at the end by giving her your number. Most likely, though, you're going to get some friendly acknowledgment and a subtle message of "leave me alone, I want to read my book," and you've got to respect that and not take it as a personal rejection.

In general, I would not worry about "creepiness," per se. You're only creepy if you don't read body language and you can't take a hint – or worse, if you IGNORE those signs and continue anyway. The quintessence of creepy is not respecting other people's boundaries.

Anyway. There's just a lot of uncertainty in approaching someone in public, so you have to kind of err on the side of assuming "thanks but no thanks" unless you get some pretty strong positive confirmation. As long as you are doing that, I don't think you qualify as creepy.

So in light of all that, online dating actually seems great for you. One advantage with online dating is that by the time you meet up with a date, you have gotten the first difficult hurdle over with – you KNOW you are both single and interested in dating, at least theoretically. This entire problem you've posted about is now moot. Furthermore, you can pre-screen your dates to make sure they're into the stuff you're into.
posted by deathpanels at 2:53 PM on May 11, 2016 [2 favorites]

Oh also, never hit on or ask out wait staff, bartenders, or anyone else who is working the venue. They have no choice but to be nice to you and it's unfair to waste their time while they are supposed to be working. They also can't leave if you're making them uncomfortable. Also they've been hit on 1,000 times already that night and are so, so sick of it.
posted by deathpanels at 2:57 PM on May 11, 2016 [22 favorites]

Yup. Even on okcupid I'm not listing a lot of my real interests, because then I'm snobby and no one knows what to talk to me about. I don't have the time or inclination to pick out the musicians that are obscure enough to signal how cool I am but well known enough to not be intimidating.
posted by jeweled accumulation at 3:11 PM on May 11, 2016 [7 favorites]

Honestly, I'm wary of men who say they like "highbrow" things.

Even if they don't use that word, men who say they like "art films" and "philosophy" and other such things are frequently boorish. They often have something to prove, and they'll use me (by sharing their opinions at length) to prove it.

In my experience, men who like these kinds of things but don't have something to prove (a) have other, less "impressive" interests as well, and (b) phrase their interests differently. They don't like "philosophy," they're readers who like to learn new things. They don't like "art films," they like independent movies. This may not feel like it's 100% an accurate description of your tastes, but it comes across as a lot less pretentious.

Oh, and they also know that liking sports and popular tv shows doesn't make them. Like, their identity isn't tied up in being only interested in "highbrow" stuff, and so other their view of people's identities don't get tied up in that either.

It sounds like what you might be looking for isn't someone who has the exact same interests and knowledge as you, but someone who is intellectually engaged with the world. That person might like "lowbrow" things. That person might like different "highbrow" things than you. This goes with what has been said about "values" above. This doesn't fit very well on a profile, but if you read for it (instead of interests) you might find some people.

Also 100% on the don't seek out women who are significantly younger, don't hit on women where they work, etc etc train above.
posted by Kutsuwamushi at 3:20 PM on May 11, 2016 [39 favorites]

Oh man. Let me first say that I am sorry for the situation you are in; I feel for you, I really do, and I can relate to a lot of what you're feeling. I apologize for not answering the question with my response. I have something that I hope will be helpful to offer instead.

I am getting a sense that you feel unbalanced and that being with a woman, the right kind of woman, would restore you and make you whole. Probably a young, pretty woman, with a sparkling personality. This is me reading between the lines, and if I am way off I apologize. Speaking from my own personal experience on a journey that is very much ongoing, I want to suggest that there may be a lot to gain from challenging these feelings and really trying to understand where they are coming from instead of chasing them.

I have a radical suggestion. Do not ask these women out. Do not ask any women out, do not flirt with women, do not ogle or fantasize or otherwise escape in your mind to a reality in which your problems are solved because there is a woman there, and instead be with the feelings of desperation and neediness that rise up inside you. There is a 'you' in there long forgotten. I see the way you are frustrated over what to do to attract people, wishing you were someone else who had more appeal, and I fear eventually you'll slowly start to twist and contort to gradually become that someone else so that you have a chance of getting this overwhelming need met. But this need can't be met with other people. It doesn't work. It just repeats the cycle. Even if you do meet someone this way you'll be hiding your true self and eventually things will fall apart, plus the pain inside will not be healed and the more you open up the more it will spill out onto those closest to you.

I just would like to be able to find someone that enjoys the ART that I do

This is a good place to start. Who is the person you are trying to find? You already know some things about her - you know what kind of art she likes; you know she is pretty (I assume); what else? What other qualities? And what happens if you find this person - how do you feel? Then what happens if you never find this person - how do you feel then? Do your emotions swing wildly between the extremes? If so, why does the presence or absence of this idea of a person have so much power over your emotional state? Who's in control of your life here?

Also, what happens if someone enters your life and shows you exactly what you want to see -- yes, I am your perfect woman -- only to suck you in and devour you emotionally? Have you noticed your own vulnerability here?

The point I am trying to make is that if you are counting on a woman to take your pain away, even a little, then you are only going to prolong your own misery and you might do some damage in the process. And until you climb out of this hole, my recommendation is that you take the focus away from others for a while, and place it on yourself. It's a good time for it.
posted by PercussivePaul at 3:22 PM on May 11, 2016 [29 favorites]

I look at online dating and don't see many people interested in the same things that I am (art films, philosophy etc). Everyone seems to be into the Walking Dead and sports.

Everyone else has covered this pretty well, but just another data point as someone who's really into ART and whose partner is really into OBSCURE MUSIC but also we watch Walking Dead (and read the FanFare threads on it!) obsessively. People are large and contain multitudes, as I'm sure you do as well, even if you don't always love admitting it. ;)

I recently have had two encounters that gave me some hope but I am unsure about how to handle them without seeming creepy or desperate.

The answer is not to try and "handle" them at all; they're encounters, like every other encounter you have in your life. They were pleasant and/or awkward experiences that reminded you of the existence of likeminded people. Now basically go about your life as if that means nothing, and maybe put together a revised OKCupid profile.
posted by We put our faith in Blast Hardcheese at 3:33 PM on May 11, 2016 [3 favorites]

I just would like to be able to find someone that enjoys the ART that I do. It is a HUGE part of my life

Which is great! You could share this part of your life with someone who doesn't know about it. (Although they might know about it, don't forget. Just because someone hasn't said as much on OKC doesn't mean they're not into it. They're interested in casting a broad enough net to meet someone compatible in other ways, so they're highlighting hobbies they think a lot of people might like.) And maybe they could introduce you to some things you're unfamiliar with, and both of you would come away knowing a bit more about life.

You mentioned OCD, and I was curious about that so had a look at some old questions of yours, hope that's ok. I think it probably matters, here... having shared interests doesn't guarantee compatibility at all, it isn't a protection against being hurt. And dating someone new will mean changes and disruptions to how you spend your time - you will have to accommodate the other person, in many ways. It will involve risk and vulnerability, all kinds of risks and vulnerabilities.

I think PercussivePaul is right - sounds like some time on your own would be a good thing.
posted by cotton dress sock at 3:47 PM on May 11, 2016 [2 favorites]

Nth-ing that you can't really know what a person is into unless you actually have a conversation with them and ask about what stuff they're into. The kind of impression you get in a coffee shop or wine store is pretty much useless on this front. And like others have said, people can be into a pretty wide range of shit, only some of which overlaps with your own enthusiasms.

One of my very good women friends is such a hardcore lover of literature that she's running four different book clubs right now; she's also completely obsessed with Dragon Age and will yell for hours with friends about which Inquisitor is going to kiss which other Inquisitor. People are complicated.

So like everyone always says about this stuff: get involved with activities that you're really into, meet other people through those activities, ask them out if you hit it off. You're overthinking this, man.
posted by Narrative Priorities at 3:51 PM on May 11, 2016 [2 favorites]

And just on the note of ART, I once dated a woman from OKC who was a former director of a major artist's museum and was then the director of a local one. I thought I was all cool because I had Banksy books and liked Takashi Murakami and had a thing for paper architecture, but she sure surprised me with an entire world of things I didn't know because I don't live in that world. None of this was in her profile!

It didn't work out, ultimately, but I still remember her fondly as a smart and clued-in person I could have been friends with under other circumstances.
posted by rhizome at 4:13 PM on May 11, 2016 [2 favorites]

Women get hit on by random guys all the time. All the time. Like so much it makes a lot of women suspicious when they have conversations with men that is just a prelude to being hit on, which they don't like!

Please consider if you want to be part of the problem or part of the solution when it comes to women feeling comfortable in public and not being regarded primarily as an object of sexual attraction.

I. E. Please consider that the vast majority of women just want to have a friendly, non-sexual conversation with a man in public with no romantic undertones,and there is robust research that demonstrates men vastly overestimate romantic or sexual interest in women.

Ask women you know well to go out with you, don't hit on strangers or near strangers in "safe", non-romantic public places. Women have the right not to be hit on at the bookstore, bus stop, restaurant etc. It is not pleasant for the majority of women I have heard talking about it, and contributes to a feeling of guardedness in public for them.
posted by smoke at 4:14 PM on May 11, 2016 [10 favorites]

I think your best bet is to develop your platonic relationships and date the friends and relative of your friends.

But if you're going to ask out a stranger, being polite and upfront about it is best and probably most effective. Don't ask out someone who is paid to be nice to you.
posted by michaelh at 4:14 PM on May 11, 2016 [1 favorite]

OP here. Ouch people!

A couple notes. I have ABSOLUTELY NO INTEREST in dating anyone that is less than 30-32 years old. I'd prefer to find someone my age and am even open to dating older women. My last girlfriend was 10 years older than me!!!

I do look young. I deal with it every day. I get ID'd everywhere I go

I would rather find a girl that I click with than someone "gorgeous"

As far as time alone, I have been alone - no dating - for 8 months. Seems reasonable to want to date again

Thank you everyone
posted by kbbbo at 4:26 PM on May 11, 2016 [10 favorites]

Reading Doctor Nerdlove is going to answer all of these questions for you.
posted by jenfullmoon at 4:26 PM on May 11, 2016 [3 favorites]

I think PercussivePaul has the right idea. I looked at your posting history and read your question about your breakup and you were clearly heartbroken. It hurt you worse than the passing of a parent--that's huge. And no judgment for feeling that way! You were together 8 years. It's like losing a limb. I've been there. I also have ADHD, depression, and anxiety and I know that for me, it takes a long time to recover from losses. I was single for two years since my last relationship before my current one. I planned on it being only a year, but I ended up loving the freedom so much that I didn't try to date for another year. It took a while to feel that way, though. I didn't get over the loneliness until we had been broken up for about nine months. And it took a while for the joy of being free to set in.

Although you are mid-to-late 30s, you are inexperienced in relationships and I'm sure that's causing you not only anxiety, but also the "othering" of women that is bothering a lot of people answering you. If your ex was the only woman you knew that intimately, it must seem like women who aren't her are really hard to understand, maybe even monolithic in their ability to intimidate and confuse. And you wonder what the trick is to talking to them. Other answers have given you wise advice. And I think referring to women as "girls" is making people think you're looking for 20-something baristas to hit on. But I noticed your ex is in her late 40s and you still called her a "girl." I would break yourself of that habit. It offends a lot of people and is just inaccurate. I wouldn't call a 30-year-old man a "boy."

I really think that relaxing and getting to know people as friends right now is something to seriously consider. It takes such a long time to get over a loss of that magnitude, and this soon after, anyone you date is going to be a rebound. I have felt the pain and loneliness you feel and you have my sympathies. But it will get better! Give yourself the gift of getting to know yourself, growing as a person, and enjoying the art and philosophy you love on your own time. I created 75 works of original art after my breakup and loved every minute of not having to worry about some man while I was doing it. I wish you all the best!
posted by Beethoven's Sith at 4:34 PM on May 11, 2016 [17 favorites]

As far as time alone, I have been alone - no dating - for 8 months. Seems reasonable to want to date again

Nobody is saying you shouldn't *want* to date yet or that 8 months is unreasonable; they're pointing out that where your head seems to be at isn't maybe the best headspace for dating.
posted by We put our faith in Blast Hardcheese at 5:09 PM on May 11, 2016 [12 favorites]

Right, I definitely wanted to date for nearly a year after my breakup--but no one I liked, liked me back and vice versa. I ended up thinking I was lucky.
posted by Beethoven's Sith at 6:53 PM on May 11, 2016 [1 favorite]

I don't understand some of the responses on here that say 'don't ask out women at stores or places your frequent' or 'you can't ask out women in daily life, only at bars,' and so on. This is a strange, cloistered, rather puritanical attitude.

You only live once, as they say. And ultimately you'll only regret what you didn't try, not what you did.

The main thing is to be as relaxed as you can, and forthright-- don't make some game or secret of it. You're a guy, you're single, you have something to offer, you're interested. Build some rapport for a while, and you feel there is rapport, just say something like, Would you like to get a coffee or a drink sometime this week? If you over-think it, you'll become more antsy about it

Screw what some people or some cultures think. None of it will mean anything when we are elderly, or dead, in the scope of the mind-bogglingly long timeframe of the universe. People meet their significant others in the unlikeliest of places. Maybe a few women will think it odd-- that's their conditioning and problem-- and the third will become your next girlfriend
posted by cotesdurhone at 7:33 PM on May 11, 2016 [3 favorites]

I'm having second thoughts... you've had a lot of recent losses. It is *probably* not an ideal time to date. On the other hand, it's what you're being moved towards right now... it's ok to not want to be lonely; there is never a perfect time; none of us is perfect. If we all waited for an *ideal* time, no couples would exist.

I do think it might go easier for you if you can treat it as an experiment - as just *getting to know* different people - and try not to get super invested in the outcomes. And if you reach out to old friends, and try to make new ones at the same time, so that you don't load these dates up with expectations that are too heavy, for the other person and for you. Think about keeping it light - it's just about meeting new people and talking to them.

Ok so, I think you are at a bit of a disadvantage for meeting people face to face, because A) you're a guy (rejection rate will be higher than it would be for a woman - that is probably also true for online dating, but that might be be less difficult to manage), B) the anxiety, and C) those two things combined - approaching people without triggering their creepdar because of a bit of (totally understandable!) awkwardness might take a lot of practice, since you're not used to it. Which is ok, too, and you should try it if you're up for it, but I'm thinking it might be a bit much right now. If you do try it, just don't take rejection personally. Most women are not going to respond to being approached out of the blue. Trying the targeted activities, as people mentioned, is a better idea imo.

I think online dating is your best bet right now, because everyone who does it knows exactly why they're there, no approach is necessary. (Well you would send a message, but there's less involved in that than in walking up to someone or whatever.)

As sockermom suggested, answering lots of questions will probably boost the likelihood of compatibility on at least some important factors. You can filter out people who don't match your values. Again, people who are into art are probably not going to be talking about it a lot on their profile, but it will probably come up in their answers to those questions.

Maybe, write up an OkCupid profile and come back for some feedback next week. (I think you are maybe not coming across 100% right now. E.g. the "girl" thing, that definitely has to go. Some of the assumptions mentioned in this comment are ones a lot of other people might make. You sound like someone with a genuine interest in art and philosophy, but the way you write about this makes it seem like it's a front of some kind. There might be some little things like that that people could help with for your profile.)

Good luck.
posted by cotton dress sock at 7:38 PM on May 11, 2016 [2 favorites]

Asking is fine, asking while at work is a fine line to walk. The creepiness usually comes in with the handling of rejection if they say no. If you are cool with them saying no, willing to think well I gave it a shot & still be polite & civil & just as friendly to them afterwards then feel free to ask. Make sure it's something small like "hey do you want to grab a coffee sometime" style of thing.

If you are the sort of person to get angry, turn on them, keep asking, stalking them, be unable to be civil to them from then on or storm off in a huff cursing all women just because they said no then you're going to be creepy.

Knowing if you have a lot in common before you ask someone out isn't really necessary, though knowing you have one or 2 things is handy not compulsory. That's the point of dating, you're "trying people on for size" as it were. Getting to know them, getting to find those common points of interest. If it doesn't work out, hey you made a friend & did some things & had some practice with dating.
posted by wwax at 7:48 PM on May 11, 2016 [3 favorites]

I don't understand some of the responses on here that say 'don't ask out women at stores or places your frequent' or 'you can't ask out women in daily life, only at bars,' and so on. This is a strange, cloistered, rather puritanical attitude.

Or... Women don't want to be feeling pressured to deal with the unwanted attention of men in their daily lives. Our time is not a public commodity. Double icky if it's a place of employment where a woman has to be there and often had little or no recourse when receiving unwanted attention.

Of course there are men that still do this. And it's gross. But on top of what I said above, the poster asked how not to be creepy- trying to hit on women who are just going about their lives is one way of getting placed squarely in the creepy box.
posted by [insert clever name here] at 8:33 PM on May 11, 2016 [30 favorites]

Eight months after an 8 year relationship with someone you planned on marrying? Obviously, you know what is right for you and how you feel. But maybe, take a bit more time? It's great flirting and all and meeting new people. Having an online dating profile could help. Online dating and Tinder/Bumble and whatever other sites people use could help you get yourself out there. As for hitting on women in public, nthing only if it's in a social space that is expected behavior, i.e. club/bar or she seems interested and is talking to you.

Not because they are being nice, but if they are flirting back. Someone mentioned body language, that will help. I have spoken with men and was genuinely interested in the topic (gaming) and was glad to have someone to talk about stuff like that with. That does not mean I am interested in them. So if a woman talks to you, it's just talking. If she flirts back, then yeah see if she wants to go out for coffee or give her your number.

Put yourself out there, but rejection is real. Don't let it discourage you. However, don't let dating and finding a significant other be the only thing you think about. There is more to you and your life than just finding someone else to share it with. Do stuff for you because you want to and there is no time like the present. Also, I get that you like art and stuff and want someone to share that passion with. Be like the woman with the 4 book clubs and do musuem tours or find some activity that you can still engage that part of your interests.

Hell, I love anime and space, do you think I go around talking about black holes and dark matter to anyone I meet? When people talk about The Walking Dead am I changing the topic to Trigun or DBZ? There's more to you than just that. There's more to women than what you think. Not everyone is the same. You will find someone that will share in your interests, but you also have to be willing to share in their interests as well.
posted by lunastellasol at 8:44 PM on May 11, 2016 [1 favorite]

Adding my voice to the ones saying take some more time off dating. A rule that was suggested to me in high school was "be single for as long as you were in the last relationship." That's pretty ridiculous on an adult timeline and eight years of being engaged, to be sure, but it can give you perspective on how long eight months actually is.

As a fellow single person looking for smartypants people of rarified tastes, lately I've been thinking of making more use of event mailing lists from local colleges and universities. I was happy in grad school. Why not spend some socializing time at campus cultural events? And don't go looking for dating, just go looking for friends.

Having followed advice like PercussivePaul's, I'm finding that for the first time in my life I'm genuinely happy and comfortable with the idea that I might be single for a long time, maybe even the rest of my life. That's a better place to start from, just like you want to be applying for jobs when you already have a job and you don't want to go grocery shopping when you're hungry. Get comfortable with yourself, first.
posted by gusandrews at 8:55 PM on May 11, 2016 [1 favorite]

You only live once, as they say. And ultimately you'll only regret what you didn't try, not what you did.

The concern is not his feelings.
posted by praemunire at 10:15 PM on May 11, 2016 [17 favorites]

I apologize again for continuing to not answer your question, but I really do think I see something that you are missing.

You posted a previous question after your breakup feeling lost and having to 'start your life over' after eight years. I can relate to this feeling because my own marriage has just fallen apart and when it shattered I had the same feeling - "now what". I looked around at who I was when I was not partnered and I was kind of nobody. I had lost touch with my own interests, my friends, my hobbies - my own story. I didn't know if I should stay in my current city or what. Everything was in doubt. And I didn't even really know who I was.

I felt such a strong pull to find the next woman. It's what I've always done in the past; one relationship ends; be shattered for a while; look for the next. In the past I never even considered not doing it. But aside from the fact that reconciliation might still be a possibility in my case, this time I felt a finality to my situation, like I had crashed and hit bottom and knew I could not keep doing the same thing. I noticed this time how I was using the idea of the next relationship as an antitdote for pain; how crushed and sad and alone I felt and how the soft embrace of a woman seemed like it would take it all away. And, also, how bringing that neediness has overwhelmed and really hurt my past partners. I was able to step beck and see the pattern this time and I felt a certainty that if I moved on to the next it would lead me back to the same place. Now, you are not me, I grant, this is me taking a leap, but I see so much of myself echoed in your story and I really doubt it's all coincidence.

If your relationship ends and you have no life - if you don't know who you are - if you find you have to rebuild your life again from the beginning - it speaks to a deeper pattern. Your life story should not stop in a relationship only to be picked up where you left it years later. It should continue; you should grow and develop and be building things while partnered; this should be fundamental to the partnership. If your life stopped, it means you threw your life aside and made the relationship your life instead. And if you did that, it means you are somewhat like me, and there is something about love and relationships that you desperately need, so much so that you will throw your own life away in their pursuit. Are you aware that this happened? My fear for you is that you will do it again. You should have your own life; any relationships that happen should grow organically from inside it. All of deserve this, but I'm genuinely worried for you.

I have more to offer - MeMail me if you want to hear it.
posted by PercussivePaul at 1:16 AM on May 12, 2016 [12 favorites]

I dunno, like cotesdurhone said, ask away.

dont see it as particularly creepy or bizarre to ask any adult casually if they wanna grab a coffee?
posted by speakeasy at 9:05 AM on May 12, 2016 [2 favorites]

One way to ask someone out without seeming creepy is to hand her your business card and say that if she wanted to call you sometime, you'd be delighted.

This puts the ball in her court, gives her information on you (so that she can google you or ask around or whatever) and doesn't require her to answer you then or give you personal information about herself. This also lets her text or email.

You could make this more personal and less pushy by saying something like, "It seems we have similar taste in music/art/wine. Here's my business card. If you were to call me some time, I'd be delighted. If you don't, that's fine too."

It tells her what you see as the connection. So avoid saying things like, "I find you really attractive/intriguing/etc." What could she possibly do with that information? She'll picture you starting at her, or waiting for her to say something "intriguing," which sounds like you're really waiting to see her undress. Ugh. If you are specific about what you might actually be able to talk about or do together, it's easier for her to picture what might come of that call, should she make it.
posted by Capri at 1:28 PM on May 12, 2016 [2 favorites]

It's fine to ask. There's no rule against asking.

But know that you'll almost certainly be turned down, because most women don't want to go on a date with a complete stranger they know nothing about and have no common ground with.

It's better to ask out someone you've spent some amount of time with before or conversed at length with.

Also, there is a rule against being a jerk about it when they turn you down. You're not protected from the outcome of your actions.
posted by Sara C. at 1:41 PM on May 12, 2016 [2 favorites]

I'm going to clarify what I said a little. Obviously, don't ask immediately if you haven't established any kind of rapport or mutual interest. You should feel as if this exists. If it does, than ask away. To echo speakeasy: 'don't see it as particularly creepy or bizarre to ask any adult casually if they wanna grab a coffee'

Plenty of women (just as men) would ultimately be glad to meet someone they find interesting and attractive in daily life.

I may get lambasted for saying this on this forum, but I've spent time and lived in various countries, and a lot of the cultural constraints and taboos being bandied about here reflect a certain narrow American attitude (of course, which is prevalent in one strain of society and not all people accept). Not only is this kind of behavior completely acceptable in many countries, if done respectfully, maturely, and tastefully, it is encouraged as a primary way of meeting a romantic partner!
posted by cotesdurhone at 1:48 PM on May 12, 2016 [2 favorites]

You have so many answers from people here saying "Ew gross, don't hit on people in public man That's creepy! Someone isn't going to go out with you if you just say "hey - I like that band too!"

But in a question whereby someone might ask "How do I ask someone out on a date?" there are a million responses saying "Hey - you've just got to start talking to people! See a girl wearing a t-shirt of a band that you like? Go and tell her how much you like the band and start a conversation from there!"

Personally, I read your question and thought you're on the right track completely. I think you'll be fine doing what you're doing. I once had a roommate who wasn't (IMO) very attractive, but he was SUPER successful with women because he was so confident. He would just talk to anyone and he was very witty and funny and made you feel the things you were saying were important to him.

I admire your confidence, you obviously know how to 'do' relationships, keep on doing it and you'll find someone again!
posted by JenThePro at 2:49 PM on May 12, 2016 [4 favorites]

My recommendation as a 32 year old woman who is actively dating:

It sounds like you are thinking really, really hard about this. You are making lists and tactical assessments. That's natural given how long it's been since you dated - in many endeavors feeling prepared helps performance - but going too deep into that space when dating can backfire. People sense when they are interacting with someone who is not fully present, and over-planning will distract you and hinder your ability to authentically connect with people. Have you ever practiced a conversation because you were nervous? Most of us do it and never get the chance to say any of the points we had lined up, largely because our counterpart does something we didn't anticipate. And why didn't we anticipate it? Because that preparation is not about the other person. It's about us - our own fears and insecurities. Even worse, being self-conscious and trying too hard to not come off as something, whether it be creepy or needy or any other number of unattractive qualities, will often have the opposite effect and create the exact vibe you are trying to avoid.

I will echo those above who vote for online dating. It takes many unknowns out of the situation. Plus, if having specific interest alignments is really as important to you as you are claiming, the likelihood that your intended will have that interest seems higher in the scenario where they openly claim to like those things in print verses the one where they were pretty and in the same wine store as you.

So, here's the actionable advice: keep it simple. Be straight-forward and respectful. Polite. Show interest. Ask questions and listen to answers. Make an effort to get to know who these women are and connect with them. At the end of the day, it comes down to chemistry and compatibility. You can't force it - there will be misses before you find a match and that's not because of some tactical error. The ones who don't work aren't a match and you need to keep looking. Eventually something will stick.
posted by amycup at 12:25 AM on May 13, 2016 [3 favorites]

What these three last peeps said.
And want to add a few thoughts

There seems to be this tendency for people to be like, hey when you have all your emotional life & issues sorted you're good to go and ready to join the human race – until then, have fun in therapy. End of. I kind of agree, if you're abusive/abused or have some crazy dependency on heroin (get help)/other, but at the same time I think its bs. You can't just put life on hold, dude you won't have anything sorted until you're like kicking it in a old folks home. I think going out with a groovy lady that you find cute will do wonders for your anxiety (ha maybe both ways). But in truth, I saw this documentary years ago, and I can't remember anything much about it (my brains remarkable like that), but for one part, it stayed with me. There was a dr working with MSF and he was talking with these young men studying medicine, and they were survivors from the Rwandan Genocide. And they asked him, how can we help people heal, if we haven't healed ourselves? And the doc said, this is a false framework that people operate in – you do not need to be whole in order to help people. And i agree. So I guess what i'm going for here, is that if you feel you're ready to take the plunge and go out with a lady, go for it, while remembering you probably have some baggage, be mindful of it, don't let it make you think you're somehow flawed. We all have baggage. Just take it slow.

And as to how to approach a female human in a non creepy way (the dog needs to pee, so I'm typing quickly, pls forgive if this whole thing comes off real blunt) some small pointers >

- music is a delightful way to connect! I burned my now-husband, then just a cute guy i really was into, a CD and came off a total dork and dinosaur, but he later told me he listened to that thing all the time. Music is such a chill way to connect, ask if they wanna go browse vinyls (if you're a dirty hipster) or see a gig like "hey did you hear that obscure band is playing in bar x next week? I was thinking of going!" Leave it open-ended, it doesn't have to be all serious, and there's a graceful exit for both of you if she isn't interested

- don't stare, no heavy mouth breathing, no really long weird silences (all creepy, unless you're both Finnish)

- timing! common sense! don't approach like if their manager/friend/other is screaming at them

- i believe you got this. Be yourself, you seem cool. Be kind and attentive and keep a sense of humor. They're just people (women). My creepy encounters run in the dozens, and they all involve stuff like turning everything into sexual innuendo, not listening to a single thing i say (NO i don't have a phone, it fell into the Grand Canyon, nup, can't be reached), not giving space (physically, mentally), and unwanted touching (WTF?!) and crying about the ex (maybe not creepy, just really, really uncomfortable)

Ok, i'm finally done and out. Good luck, man!
posted by speakeasy at 1:00 AM on May 13, 2016 [6 favorites]

I realise this thread is from nearly 10 months ago, but after reading this and some of your other questions I wanted to add an important caveat to what seems to be frequent advice to join/start Meetup groups as a way to meet ladies.

Of course you want to meet women who share your interests, preferably in a low-stakes, informal setting, and Meetups CAN be a good way to do this--totally normal, not skeezy in and of itself and not at all a bad way to go about it. However, I want to point out that women, especially younger women (I'm a 27-year-old ladyperson FWIW) can figure out pretty quickly if you are in the Meetup exclusively or even primarily for this reason, and it can be a major turnoff even if the man in question is otherwise relatively cool/attractive/whatever. (This is in large part due to the need to protect oneself from people like this, unfortunately.)

Why should this be so offputting, especially when you're not trying to do anything inherently predatory or shitty? Because--and you ought to keep this in mind when approaching people you meet through these activities--the vast majority of these women are not there to meet men. (A few certainly are, but those cases will usually be obvious.) Most of us genuinely want to find a space, be it a board game night, a rock-climbing group, a book club, whatever, to indulge in and discuss activities we enjoy, without being subjected to romantic / sexual advances (which, if we rebuff them, can quickly become a source of resentment and awkwardness within the group).

When a man does, in fact, use the context of the Meetup to ask us out or otherwise proposition us, if there's not already a clear foundation of real camaraderie it can feel like a huge slap in the face: I thought you were talking to me because we both connected over [Maupassant, whitewater rafting, whatever], when in reality you were pretending to take me seriously as a person/geek/fellow fan so that you could get in my pants. (This goes double for the brainy, high-brow types you seem to be looking for--ask me how I know.) Other women might feel differently, but for me and the women I know in my various cultural/Meetup-y type activities, this frequently feels like a manipulation tactic, and can and will lead us to shut down people we might otherwise have found attractive.

I say all this not to criticise or discourage you but to try and help you steer clear of something I've seen repeatedly torpedo the chances of otherwise decent guys trying to pull this off. It essentially comes back to the whole "treat women like people" rule:
- if it's a group you frequent regularly, try to stick to women you actually like as people (we can tell),
- who seem reasonably receptive to your overtures,
- and to whom you'd actually be interested in talking even if they were not romantic/sexual prospects.

If she isn't feeling it, back off and (this is important) resume interacting with her normally.

This approach has two advantages: it increases your chances of success (perhaps by being more selective about whom you approach) and avoids saddling you with a capital-R reputation that could hurt your chances with other female members (or even the same ones) down the line, should you strike out initially.

You sound like a decent guy whose heart is in the right place. From a fellow picky smart person, good luck!
posted by TinyChicken at 11:18 AM on April 9, 2017 [1 favorite]

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