A friend I met online asked me for a primer on how dating works. I’m really not the person to ask -I don’t have a great deal of experience in this regard. But my friend has less, so I said I’d give it a go. I’ve pasted my response here– does this stuff seem to have merit? Is there anything you’d take issue with?
Friend,
Honestly, I’m not all that great with women. You’d be well-served to take my advice with a generous pinch of salt. However, I do get dates, and there are things that seem to work for me, which I’ll talk about here.
The most important thing for you to realize is that, to a really surprising extent, the ways in which you’re messed up don’t matter. It doesn’t matter that you think you’ve got crap social skills, or that you’ve never been in a relationship, or what have you. Oh, they matter to you – you can remember every time you couldn’t work up the nerve to ask a girl out, or lacked the savvy to realize she wanted you to, or a girl told you that you made a fantastic friend. But I promise, there isn’t a giant, blinking “failure” sign flashing over your head. When you sit down for drinks with a girl you’ve never met before, she doesn’t know a blasted thing about you – she doesn’t think of you as strange at all. In fact, if you’ve met her online, and she agreed to meet you IRL, she wants to like you. She’s there because she thinks you seemed nice, interesting, probably cute – and it’s human nature to want to be right. That woman is looking for reasons to like you.
I’ll talk more about that in a minute. But first, let’s talk about how you get to drinks with that woman in the first place. As I mentioned above, meeting women online is a good option. There really isn’t a stigma attached to it any more (if ever there was), and meeting women online plays to your strengths: You can think, and you can write. You have time to do both, and you’re doing them from the comfort of your computer. So, join an online dating site. I recommend OKCupid – it has a large userbase, it’s free, and it’s worked well for me. But any site will do. Just complete your profile, taking care not to say anything self-pitying. Try to be funny, if you’ve a knack for it. And make sure you include at least one good photograph – it’s technically optional at most sites, but leaving it off is a terrible idea. This shouldn’t really be a photo you take yourself in the mirror – try to find a photo of yourself having fun, maybe from a vacation.
Once you’ve got your profile set up, start looking at the profiles of the fairer sex! The trick isn’t to simply send messages to the most attractive women – though, of course, you don’t want to message anyone you think you wouldn’t be attracted to. What you want to do is actually read the profiles, and respond when you see something that actually triggers an amusing response. You know how you snark or joke on friends’ Facebook wall posts sometimes, or post a related link, or something like that? Same deal; if a woman says she likes zombie movies, maybe you ask her whether she prefers fast or slow zombies. If she replies, you can talk about why you like fast/slow zombies, and maybe about something else on her profile, and so on. These messages are conversations, so start them when you’ve got something interesting to say.
Unless you’re some sort of Adonis (and possibly even then), you won’t get a response most of the time. This isn’t because you’re coming off wrong; that’s just normal. Pretty girls on dating sites get a lot of messages. Keep at it, and eventually you’ll get hits. When you do, don’t just keep tossing messages back and forth forever. You’re not looking for a pen-pal, nor are most of the women on these sites; if you’re hitting it off, you can ask a woman out for drinks after a few days, or even after a single day. (I just came home from a second date with a woman I asked out for drinks a couple hours after “meeting” her online).
Unless you’ve got problems dealing with alcohol, I do recommend grabbing drinks as a first date. Drinks can last as long as you’re having fun, but dinner takes too long if you aren’t hitting it off. A movie or concert doesn’t give you enough of a chance to talk. And coffee tends to make people tense – the relaxing effect of a drink or two (don’t get drunk!) is more conducive to a fun first date. You can – and should! - try for different ideas for dates later on, but there’s a reason drinks are a cliché first-date thing. If you want to stand out, find a bar your date probably isn’t familiar with; whenever I’m taking out a woman who doesn’t know DC well, I suggest a “speakeasy” bar that doesn’t have any street-front signage. Very good drinks, and my date learns about a new place she’ll probably like; people enjoy doing that.
So, you’ve asked a girl out for drinks, and she’s said yes. Nicely done! What do you wear? When in doubt: a solid-colored, button-down dress shirt and dress slacks. You really can’t go wrong with that. If I’m going to a higher-end bar (like the speakeasy mentioned above), I like to wear a suit; suits look good, which helps keep you feeling confident. If you don’t like suits, though, then you don’t need to wear one, and for most bars you shouldn’t. You do need to wear a dress shirt and slacks, though. Clean and freshly ironed; even if they’re machine-washable, your best bet is probably to just drop your clothes at the dry-cleaner the day before.
Now you’re at a bar, and you’re actually sitting down with your date. And right away, it’s awkward. You’re nervous, maybe she’s nervous, and you can’t think of a damned thing to say. This is awful!
Calm down. Of course this is awkward – you’ve never met this woman before in your life, a few online messages excluded. It’s okay that this feels awkward; it doesn’t mean you’re screwing up. Just say something – ask her how long she’s been in your city, say, and talk about how you ended up there. If there’s a funny story involved, tell it. Odds are pretty good that things will get less awkward fast – people like talking about their lives, and the conversation will tend to drift to other things naturally enough. If you’re hitting it off, this will be fun. You might not hit it off – again, this doesn’t mean you’re doing anything wrong. Most people just don’t click. You can go back to OKCupid (or whatever site), and try again. But the odds are that, even if you don’t click, you can get a decent conversation going. Remember - this woman wants to like you, and she’s trying just as hard as you are.
If you are hitting it off, you might consider making a move. Don’t take this too far on a first date; there’s a lot to be said for being what is termed, quaintly, “a gentleman.” But gentlemen aren’t eunuchs, and your date almost certainly isn’t looking for a eunuch. This is, after all, a date. If you’re actually attracted to a woman, you need to let her into your personal space. If you’re sitting next to her, and she slides closer to you, don’t slide away! For that matter, maybe try sliding closer to her; don’t trap your date against a sofa arm-rest, but if she seems into you, perhaps get a bit closer. Maybe rest a hand on an arm or leg. Judging when a woman is into you is a hard thing to describe, and I’m not that great at it to begin with – but she might be touching your arm a lot, or laughing at your jokes, or leaning in closer to speak than is necessary. If you think your date is into you, you might as well act on that belief a little bit; if you’re wrong, she’ll move away, or even ask you to knock it off. Not the end of the world, so long as you’re not being a boor and groping the poor woman; people get signals wrong all the time.
Do you kiss the girl when your date is over? Depends, but I’d say “Probably not,” unless you’ve had an amazing time and really *want *to kiss her – in which case, there’s at least a chance she might want you to kiss her, too. If you read her wrong, again, not the end of the world – even if the date went really well, she might just give you her cheek, or say she’s shy (I’ve had both happen), or what have you, but it’s not likely you’ll deeply offend a woman this way. (I wouldn’t try it at the end of a bad, or even lackluster, date, though. Only if you’ve got some real chemistry going, or at least honestly think you do.)
Finally, you’ll go home. If you think you want to see her again, ask her out again. Wait a day or two, first.
You can do this stuff, man. Seriously.
