How do I flirt with guys I meet from OKCupid?

July 17, 2012 12:24 PM

How do I flirt with people I meet from OKCupid?

I'm a female in my 20s. I was in a really serious LTR for a few years, we broke up, and I took months off from dating. Recently, I've gone on a few OKCupid dates.

I know how to flirt with people. I flirted with my boyfriend. If I meet a guy in real life and it's clear that he's attracted to me, I can flirt with him just fine. My problem is that I really don't know how to flirt with people when I don't know if they're attracted to me or not. Or in situations where I don't know if the person is into me in a romantic way.

Part of that is self-consciousness but part of it is also that I really hate the idea of making a guy feel uncomfortable and awkward, especially in a situation where he might feel the need to be polite. If the guy is the one who suggests meeting up, I still feel weird flirting because he might meet me in person and not be into me. If I'm the one who suggests meeting up, then I feel even more cautious about it. Plus, partly I always suggest meeting up just to talk and get to know each other, not "Will you go on a DATE with me" just because that feels more pressure-free and comfortable for both people.

Anyway, what ends up happening is that we go out and have an awesome conversation over some beers and really like each other as people. And have NO spark of attraction whatsoever. No flirtation. No hint of sexuality. Like we're just two completely platonic buddies at the bar. And neither of us ever contacts the other again.

I would really like to change this because I have a date coming up with someone who seems really cute, smart, and interesting. I would like to get over my issue and really date him. So I would like to be able to flirt on my date and introduce that element of a romantic spark, and not have it be sterile like the other ones.

How? What should I do? I need some things I can do that won't be too overbearing (both for my sake and his, he seems a bit reserved) but still introduce that element.

posted by Sock of Silliness to Human Relations (21 answers total)

Call them for a second date
posted by MangyCarface at 12:25 PM on July 17, 2012 [2 favorites]

um, you're on OKCupid, looking for a relationship, meeting other people who are looking for a relationship for a date. What makes you think that the person you're meeting would be uncomfortable if you flirted with them? I would think it would be more uncomfortable to meet someone in an obviously romantically-charged situation and NOT flirt with them.

Considering that most people flirt with people in casual situations without even knowing if they're single or looking for a relationship or anything, I think you're overly concerned about this.
posted by treehorn+bunny at 12:31 PM on July 17, 2012 [3 favorites]

I really hate the idea of making a guy feel uncomfortable and awkward, especially in a situation where he might feel the need to be polite.

I am struggling to think of an occasion in which a guy would be made uncomfortable by a bit of friendly flirting, especially in a dating situation. Heck, most of the straight guys I know don't mind being flirted with by gay guys. Even if you are not interested in the person, it's still flattering.

Light touching (knee, upper arm, shoulder), steady eye contact, uninhibited laughter, close physical proximity, are all lovely ways to signal your interest.
posted by Rock Steady at 12:33 PM on July 17, 2012 [5 favorites]

The same way you flirt with anyone else. If anything, you've got two extra assurances:

1. Less chance of friend-of-a-friend weirdness if things don't work out. (Emphasis on "chance" - you will likely learn soon just how small the world is - but still.)

2. More-or-less assurance that they are single and interested enough to meet up.

If this seems facetious, it shouldn't; if anything, it's harder to get the read the other way around.
posted by dekathelon at 12:35 PM on July 17, 2012

It's easy to flirt with people whom you know are already attracted to you because it's low risk and you know you won't get rejected. Flirting with people whose attraction you are unsure of can result in a horribly awkward experience, so it's natural that you would be hesitant to do so. This doesn't mean you are shy or socially awkward - it just means you respond to high-pressure situations as most rational people would.

One tactic that I have found that worked really well for me in the past was to use double entendres that can have either an innocent meaning or a sexual connotation. If the other person doesn't seem comfortable in their response, I act like my meaning was perfectly innocent. If they pick up on the sexual cue and respond in kind, then I know that it's "on" and they're attracted to me.
posted by wolfdreams01 at 12:38 PM on July 17, 2012 [1 favorite]

Light touching (knee, upper arm, shoulder), steady eye contact, uninhibited laughter, close physical proximity...

Bingo. You can be talking about the stock market or some equally-unsexy-to-the-general-populace topic, but if you make eye contact when you smile and laugh, and lightly touch his hand or shoulder to make a point, it's a word of difference from just conversation.

Also, you can go to a place that has couches so you have to sit next to one another rather than across from one another. You can start off with a respectable amount of room between the two of you, but it's all that much easier to close the distance if you're not sitting at a table.
posted by griphus at 12:38 PM on July 17, 2012 [1 favorite]

Response by poster: um, you're on OKCupid, looking for a relationship, meeting other people who are looking for a relationship for a date. What makes you think that the person you're meeting would be uncomfortable if you flirted with them?

Just to answer this one question, in the profile of the new guy I'm about to meet, when it says what he's looking for, he only has "new friends" listed. There are some indications he would be open to dating, but I'm nervous to assume that's the case. Does that change anything?
posted by Sock of Silliness at 12:39 PM on July 17, 2012

If you're looking to meet someone to date, try to stick to people who have openly declared "I am dating." Otherwise you're a week or two from an AskMe question about how you can't figure out where your relationship is going and whether it's even a relationship or not.
posted by griphus at 12:41 PM on July 17, 2012 [10 favorites]

Just to answer this one question, in the profile of the new guy I'm about to meet, when it says what he's looking for, he only has "new friends" listed

This is the worst- a ton of people on the site are waffling around in that obligation free 'new friends' search-zone. I would specifically ask him on the first date, and if you get an underwhelming answer, he's on there for either lazy hookups or some sort of confidence boost.
That said, it is the default option for new profiles, but if he's too dumb to figure out how to change that he's an idiot anyway
posted by MangyCarface at 12:42 PM on July 17, 2012 [3 favorites]

I would ask him before you meet him, because you are looking for a date and don't need to waste your time if he is not. That said, OKCupid is a dating site, and contacting someone on a dating site is roughly equivalent to saying 'can I buy you a drink?' in a bar. It's theoretically possible they did it without being attracted to you, but if they did then it was their responsibility to make that clear, because the default assumption is that they are hitting on you.
posted by jacalata at 12:47 PM on July 17, 2012

There's something awkward about a blind date. You're both sort of on the spot to decide whether the other person is worth a romance. You get face to face too fast in a blind/internet date.

If I were ever to date again, perish the thought, I'd try to set up dates where we were doing something rather than bar or dinner dates. If you go see the animals in the zoo, or shop for antiques, or go kayaking, or whatever, it's easier to flirt because you're not on the spot.
posted by musofire at 1:00 PM on July 17, 2012 [2 favorites]

The people on OkCupid who just have "new friends" listed, especially the guys, are still looking to date. If you guys are meeting in person, it's a date. My experience has been that the number of single people who are actually using OkCupid to find friends is vanishingly small.
posted by Ragged Richard at 1:03 PM on July 17, 2012 [2 favorites]

he only has "new friends" listed. There are some indications he would be open to dating, but I'm nervous to assume that's the case

Are you sure this guy is unmarried, unattached, single, or in a mutually-and-consensually-so open relationship? The way it is phrased here looks like a lawyerly way of leaving wiggle room when you find out otherwise ("the profile did say I was only looking for friends!"). Tying it back into the actual question, it's potentially flirty and definitely acceptable to address the question head on:
"You're so awesome, how are you not taken yet?!"
"Isn't your other girlfriend going to be wondering where you are?"
Smile or add a ;) as appropriate.
posted by whatzit at 1:16 PM on July 17, 2012

Meet people in person, as quickly as possible and flirt in person. One mistake people make is to have long, drawn-out email and IM relationships and put off meeting. Huge Mistake!

Be yourself, you want to be as comfortable as possible. If you feel uncomfortable, write it off. If a guy isn't down with your flirting, he's not for you. Next!

The way to deal with dating sites is to meet as many eligible people as possible, as quickly as possible.

Don't audition for people, hoping they'll dig you. If someone looking for "friends" contacts you, say very explicitly, "sorry, I'm looking for dates." Why would someone put "Looking for Friends" on a dating site? That's "hit it and quit it" guy. He's looking for casual. If that's cool with you, you're on notice. If you want a relationship, not your guy.

Dating sites are just a way of casting your net wider, especially OK Cupid (there's no bogus claim of compatibility, just pictures and profiles.)

First talk to guys on the phone. You can weed out 70% of the creepsters that way. Have a standard way to end the call, "I really appreciate your speaking with me, you seem nice, but I don't think you're right for me. Have a good one!" If you DO like a guy, invite him on a short, coffee date, with specific expiration time. "You know, I have an appointment in this part of town on Thursday. Want to meet me at Starbucks between 5 and 5:30?" Let people know that the introductory date is just that, "Let's meet briefly to see if we're into each other and go from there." Only make a second date is you're truly interested.
posted by Ruthless Bunny at 1:22 PM on July 17, 2012 [3 favorites]

One thing that strikes me about your question is that you seem to be hung up on whether the guy is interested in you, and the stuff about your interest in him (at least the guy you're about to meet) is what you've picked up on from the profile, before you meet in person. I don't get the sense that any of these guys have turned out to be worthy of YOUR interest upon meeting. So I think it's a matter of meeting the right guy.

My read is that the spark isn't happening because of something you're failing to do; it isn't happening because it's a rare thing, and even if there WERE something you could do, and you figured out what it was, you'd continue to feel frustrated meeting dudes who didn't perform the mystical spark-creating gyrations you were suddenly performing, which is to say dudes like the dudes you're meeting now, who simply aren't getting your motor running.

Okay... At the risk of contradicting what I just wrote, I will say that to think of flirtation or other expressions of romantic interest in terms of their potential to make the other person uncomfortable is to dwell on the negative, and to catastrophize. Your better mindset is that you are DOING SOMETHING THAT STANDS TO MAKE THE OTHER PERSON'S LIFE MUCH BETTER, because you are an AWESOME PERSON. That's the mental hack that has ridded me of my compunctions about making bold moves.

And he may wind up being uncomfortable, but so what? If getting the moves put on him by you is the worst thing that happens to him this week, he's got it pretty sweet, because I bet there are a lot of dudes who would love to be in his shoes, and this is the risk he runs by pursuing people and going out on dates with them.

Your personal happiness is way too important for you to avoid going after it because of the risk that a dude is going to get his panties in a bunch at the thought of being intimate with you, and if he turns out to be a whuss, or not into you, you'll be a lot happier finding this out by taking active measures, because there is absolutely nothing wrong with what you want.
posted by alphanerd at 1:29 PM on July 17, 2012 [7 favorites]

There are some indications he would be open to dating, but I'm nervous to assume that's the case. Does that change anything?

Flirting isn't just a fun thing to do - it's also a practical way to gauge if someone is (or might become interested). Flirt gently at first, and if he seems receptive, ramp it up a little, and if he doesn't, dial it back a little, until you can figure out if he takes a while to warm to you or is only looking for friends.

Guys get judged negatively and harshly by what they indicate on a dating site that they're open for, so I would suggest listing "new friends" is often (usually?) not firm unless the relationship status is also "seeing someone" or something like that. He might just be trying to be judged on his merits instead of the reader's prejudices.
posted by -harlequin- at 1:37 PM on July 17, 2012

So, in some ways I'm against the characteristic meet for one drink or coffee 1st OKC dates, because, as you mention, they're way less likely to end up as fun adventures, and way more likely to feel like job interviews. I've had more fun if I went to get drinks and dinner on a Friday night, with more potential to make a night of it. It's definitely higher risk, and there may be some confirmation bias going on for me, but I have a really hard time getting excited enough for the 'spark' having a beer or two at 7:30 on a Tuesday night.
posted by mercredi at 1:39 PM on July 17, 2012 [1 favorite]

Pick a bar that has bar games (skee ball, shuffle board, etc etc), or any first hang out activity that allows you to get closer and make innocent physical contact. The innocent part can become more of a flirty thing quite easily if you end up having a good time.
posted by skrozidile at 2:57 PM on July 17, 2012 [1 favorite]

I still feel weird flirting because he might meet me in person and not be into me.

What's there to lose?

A) He's into you but feeling the same way or just shy. Nothing happens and you don't call each other again. If you try flirting, maybe a spark happens.
B) He's not int you so it doesn't matter anyway.

Is there somewhere you could go afterward to watch a sunset or go for a nice walk and a cup of coffee or something? A bar is not the most enticing place for romance for some people.

Also, if you choose something you like to do or want to checkout anyway (an art gallery, something in the city, a beach) then it's not such a big loss if the date doesn't work out.
posted by Golden Eternity at 9:47 PM on July 17, 2012

Can you dress in a more flirty manner? You know, show a little more boob or a little more leg? That might be an easy way to flirt without really having to do much. And you can take a scarf or sweater, and if you aren't feeling the romantic vibe, then cover up.
posted by I am the Walrus at 1:43 AM on July 18, 2012

Another take to what's already been said - I've tried OKC, and in my experience, the site provides a meeting of the minds more than a meeting of the flesh. Our minds are capable of moving a lot faster than our bodies; meaning, there is a bridge to be crossed, to "drop in" and feel really natural in your skin with them. I echo that doing something really physical and innocent together, like bowling, or hiking, or skee ball, etc would be a great way to get into your body with this new person. If they live in another city or for one reason or another you wouldn't be likely to ever run into them by accident, this may be even more necessary because you're coming from different physical environments, and syncing up physically like this can really help.
posted by dolce_voce at 9:32 PM on July 24, 2012