January 25, 2010 2:08 PM   Subscribe

Help a late-blooming dating newbie figure out the mysteries of entering a relationship.

Inexperienced late-20s male trying to get back into the dating scene. I had some issues with shyness/introversion and fear of intimacy when I was younger that kept me from building the sort of basic dating/sex knowledge and experience most people my age have formed. I've done a good job of getting over the introversion the past few years to form some solid friendships, but dating is still a bit of a mystery, particularly the fine art of crossing over from "friends" to "dating".

One of my biggest issues is flirting - as odd as this sounds, I feel like I need basic instruction or coaching in this. Although I can sort of do this when I'm relaxed and enjoying myself, I often come off as overly serious or distant if I'm nervous or don't know the person well. In other words, when I first meet most women I'm interested in. Any suggestions to make myself more fun to be around, flirty without being too obvious, and more engaged would be welcomed.

Another issue I've had is interpreting signals. I have a number of female friends who seem to be have this playful/flirty way of speaking and writing when they talk to ANY guy - how can you tell if they're into you, or just being their usual flirtacious self? For example, a girl I recently met that I've become rather interested in e-mailed me after I gave her a ride last week, basically saying "thanks...maybe we could hang out sometime. If you're ever bored, you've got my number :)" She tends to be a bit flirty in e-mails though, which leaves me wondering if she is indirectly asking me out or if she literally just wants someone to hang out with.
posted by anonymous to Human Relations (11 answers total) 20 users marked this as a favorite
Are you able to back off if they are just being flirty without being interested? Put another way, if you expressed interest and they (hopefully gently) turn you down with "Thanks, but I just want to be friends", can you be friends with them?

Because if so, it doesn't really matter whether they're subtly asking you out or just finding someone to hang with. Ask them out to do [activity] sometime. Be yourself, have fun, play it by ear. And if it goes well, ask them out. If they say yes, great! If they say no, smile, say "thanks for being upfront", and go about being friends.

Also, re: meeting people. Try something new and go out to events. A new friend I made at work dragged me out forcibly to a D&D event and I fell in love with it. Couple of months later, met my boyfriend at D&D.
posted by Hakaisha at 2:14 PM on January 25, 2010

flirting - as odd as this sounds, I feel like I need basic instruction or coaching in this.

"What Social Science can tell you about flirting and how to do it."
posted by Jaltcoh at 2:39 PM on January 25, 2010

Here's the secret: There is no big secret that you've been missing out on. What you've been missing out on is the "trial and error" part of this whole process. Get in there, cowboy. Break some hearts. Get yours broken. You have to take risks and experiment with what WORKS FOR YOU. We can tell you how we pick people up, woo people, do the mating dance, or otherwise find companions in this cruel world. But that wouldn't guarantee that you'd have any success.

Stay alert, interpret the signs as best you can (you WILL misread some), and have fun. That's the best any of us can ever do.
posted by greekphilosophy at 2:42 PM on January 25, 2010 [1 favorite]

I have a few pieces of advice for you, as a fellow late-bloomer:

1) Friends to lovers is a difficult path, and not a great strategy. You can ruin friendships by misjudging. It is exceptionally difficult to get someone to re-categorize you once they have you pigeonholed. Most people make up their minds very quickly. Some of mine are: Friend-potential, Friendly acquaintance, Possible dating partner, No chemistry, Creep, and "Oh God No". Switching between them is usually not worth the effort. I've done it once and it didn't work out well at all.

2) Make your mistakes on relative strangers. People who don't know you well enough to have categorized you. The rejection is easier to take from people in that category. It makes it easier on your circle of friends, too.

3) You *must* approach. It is the guy's job. You have to gather the courage and ask. Most people are remarkably nice about it, especially if you don't take obvious offense. They'll just say something nice, and then you'll be out. Vast generalizing here, but it fits with my experience that most women dislike being made to give overt signals to get you to man up and just ask them out already. In other words, being afraid is one of the biggest mistakes you'll face, and the only way to get past that is to just go do it.

When most people say that women like "Bad Guys" I think they mean that (mature) women like men who have enough self confidence to state their interest, and to take the lumps if the interest isn't shared.

4) Of all the online dating services, I liked OKCupid the best. It is free, and if you take the stupid questionnaires, it really does make it easier for you and her to tell if you have any compatibility.

For example, I won't date heavy-duty committed Christians or homophobes. We're not going to be compatible. OKCupid let me filter them right out.

After you've taken several questionnaires, OKCupid gives a "match percent" between you and anyone you are viewing. If you have a 95%+ match with someone, then unless they are tied up already, they are quite likely to at least respond to your initial contact mails.

You should still approach people "offline" (see #3 above), but OKCupid will get you some dates. With a little effort, as a 40 year old, twice-divorced non-super-hunk man who prefers women in their late 20s or early 30s, I was on 2-3 dates with different women every week. That experience is just what you need.

(Met my GF through OKCupid, coming up on a year together now, couldn't be happier.)
posted by Invoke at 4:21 PM on January 25, 2010

"thanks...maybe we could hang out sometime. If you're ever bored, you've got my number :)"

She's interested. I've sent emails like this when I was interested in getting to know someone more in the hopes of the guy being interested in me. Write her back, say "you're welcome. Hey, are you free next Friday? Lets do ____" And then maybe mention something you guys talked about during the ride, or anything to get conversation going, so she still has something to respond to if she's busy next Friday, and hopefully you guys get to hang out!
posted by KateHasQuestions at 6:05 PM on January 25, 2010 [1 favorite]

If you're definitely interested in a girl, I would suggest just going for it and asking her out in a way that makes it clear that you want to be more than friends. I've met guys I really enjoy being friends with but am not interested in dating. If I even suspect that they might be into me, it makes it hard to establish a friendship without second guessing myself and worrying that they're taking my signals the wrong way. The earlier you get it out in the open (and sadly yes, you're probably going to have to make the first move in these situations) the more chance you have of dealing with it, moving on and being friends/dating/not friends.

As for the girl and email you mention in your question, personally that's the kind of ambiguously flirty thing I would never say to a guy I wasn't interested in. I would, however, say something like that if I wanted to give the guy a signal that I'm interested, and I would hope he'd pick up on it and ask me out.

This is all just my personal, 20 year old female take on this, though. One lesson you should learn, if you don't know it already, is that all girls are different.
posted by MadamM at 6:23 PM on January 25, 2010

Re: your last paragraph: since you are interested in her, just interpret it the way that you want: i.e. that she's interested. Let's play this out: if you're interested, and you assume she's interested, then you proceed accordingly. It she really is interested (as opposed to just wanting to hang out), sparks fly and you get butterflies in your stomach and you're all excited and you set up another get together/date. If she actually isn't interested, she'll probably say no to that second get together. That's when you back off, think about the whole experience and learn that this person in particular might be quite flirty, but it didn't mean that she was interested in you. And also realize that this may not hold true for the next person.

Now, if you're interested in her, hang out with her and assume that she just wants to hang out (and she's not interested in you), then you're going to interpret all her flirtiness as "she's just flirty" and prevent yourself from sending out your share of sparks so they can fly. If she was interested, she'll think "he's not interested, oh well" when in fact, you weren't open to her being interested in you, and you missed an opportunity.

Bottom line: you like her. Show her you like her; this should not be dependent on "Does she like me? Does she not like me?" If she doesn't like you, she won't want to hang out again. If she does, she will. You can keep progressively making small moves, like walking close together so your arms touch, a small hug, arm around her, etc. If you feel her pulling away from these things or if she clearly says, "I just want to be friends" - that's when again, you back off.
posted by foxjacket at 7:13 PM on January 25, 2010 [1 favorite]

OK, seriously, some people just don't flirt. I never understood the flirting thing myself, and usually when a guy blatantly flirts with me I assume he flirts with all the girls and it means nothing to me. Obviously, this isn't the case with everyone (or with most people, admittedly), but just saying that flirting isn't a requirement for getting into a relationship, and you don't need to think you must master this art of flirting or try really hard at it. Usually, when I've had a thing for a guy that I didn't know very well or wasn't sure if he liked me, I just got really awkward and uncomfortable around him, which unfortunately did not work at attracting him. What you do need to be able to do is *communicate.* Think less about flirting and more about merely talking and getting into a decent conversation with someone you find interesting.

As for how to make yourself more "engaged," I don't know. A good start would to be put yourself in a position where you and potential female interests are taking part in activities that interest both of you, so that at least would give you something to talk about, and you can take it from there.

As for that one girl, since you say she has seemed flirtatious towards you and then also said you should call her if you wanna hang out, yeah, I would say she wants you to ask her out. If you like her, you should give it a shot.

If that doesn't work out, I second OKCupid - not from personal experience with it, but because I know a non-flirting guy who had good luck there.
posted by wondermouse at 7:57 PM on January 25, 2010

You sound adorable! I'd so date you. :)

Call her and ask her to do something not-quite-datey. Lunch rather than dinner. Say you want her advice on something (birthday gift for mom, applying for a job, writing a novel, whatever you think she knows and you don't). We all like to give advice!

Flirting will just HAPPEN when you're having fun together. Guys who can flirt with anyone at all? They're usually not great dating prospects. We ladies like to think that you are special with us, not everyone with an X chromosome.

Really. Call her. Say you need to meet with her (over a meal, you pay because she's helping you) to get some advice about a subject that she knows more about.

Let it happen. If it's meant to happen, you just have to provide the opportunity. Do not worry about being cool or flirting. She already likes you. You'll laugh and have fun and be wonderful, if you just give yourself the chance.
posted by pippin at 10:52 PM on January 25, 2010 [1 favorite]

I'm the OP. I know I posted this anonymously and this thread is most likely dead by this point, but I wanted to follow up because I don't care, am honestly feeling horrible, and was hoping someone is still reading this.

I met up with the girl in question tonight and, well, it just didn't go like I had hoped. I tried getting a little closer to her, making physical contact, etc. but felt like I wasn't getting back anything. Lots of friendly banter, no red flags, but no serious contact or interest from her either. I think I've been permanently relegated to the "friend zone" at this point. I really had my hopes up - I think she truly understands my very odd/atypical dreams and desires in life (this is something that seems to be INCREDIBLY rare, and is what attracted me to her so badly in the first place) but I felt like I was struggling to find mutual attraction - to her, I seem to be just a friend and a guy to hang out with.

I know you can't go through life "needing" a relationship, but I really needed this. Particularly after everything else that's gone wrong this year. I don't know, I'm seriously starting to think that maybe I was just meant to be single and celibate for the remainder of my years :(


@Invoke - I've tried OKCupid, but my only two dates were, well weird to say the least. My last one went okay I guess, the girl was obviously into me, but for some reason I didn't feel any sort of spark at all. As weird as it sounds, I felt sort of sorry for the girl as she seemed pretty nice and I hated dashing her hopes. Guess I know the feeling all too well. I have since stopped online dating, but might try it again in the future.

@pippin - Thank you, you are incredibly kind (I mean this!). Your comments brought a very badly needed smile to my face :) It's a shame I can't find someone like you in real life.
posted by photo guy at 11:00 PM on January 28, 2010

@photo guy - My "hit rate" for chemistry in dates was about 1 in 7. Seriously, sometimes I'd have the woman back to my place, on the couch, and yet not make a move because *my* chemistry just didn't give me the juice to make a move. The mystical magical "chemistry" has to hit both of you.

Go on more dates. This is true whether online or offline. Chemistry is incredibly hard to predict, and so damn important. Keep trying and good luck. (Most) people do need relationships to be truly happy, even if you are personally (and incorrectly) convinced that you "shouldn't."

In the meantime, read "The Happiness Hypothesis". He makes that last point much better than me, with tons of real data to back it up.
posted by Invoke at 1:31 PM on January 29, 2010

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