Social Minefield: A Guide To Flirting

Even the socially adept sometimes struggle with the flirting question: how do you chat somebody up without seeming cheesy, over-the-top, or creepy? Luckily, we have some answers.

I’ve said it before — flirting is tough. You don’t want to make an idiot of yourself, and — assuming you’re a good person — you also don’t want to invade someone’s space or harass them. But you don’t want to just stare into your drink and let someone awesome pass you by, either. Here are some tips to help you seize the moment without being a jerk:

Think about making the other person feel good.

I talked to Fran Greene, flirting, dating, and relationship coach and author of The Flirting Bible, who says, “the goal of flriting is to make someone feel special.” This is great advice in itself — although flirting might lead to a date, a friendship, or a relationship, it should be less about getting what you want than it is about making the other person feel good. So if you want to have a conversation but the lady (or dude) next to you on the subway is clearly busy/not interested/creeped out, then step off. Find a situation and an approach where your attentions will actually make someone feel good, and you’ll have a lot more success.

Give a compliment, but make it a good one.

Says Greene, “The best compliments have the element of surprise. […] If you’re always complimented because of your great voice, if I say, ‘you really have a great voice,’ you’ll say ‘thank you,’ but it won’t really mean that much to you.” Something like, “you have an incredible way of listening” might be more unexpected and more meaningful.

Obviously, you can’t always predict what people get complimented on a lot, but you can be a bit original. Someone once told me I had a great attention span and I felt great for days. Katrina C. Danger of Autostraddle cautions against the overly bizarre compliment:

[M’ake sure it’s not too out there. “Hey, I like that plaid shirt” is okay. “Hey, you have really nice armpits” (this has actually happened to me) is not.

But I actually think the nice-armpits line could work in the right context, better than a generic “you’re hot.” In any case, compliments on clothing (i.e. that plaid shirt) are often a good bet — personal style is something someone chooses, so you’re really complimenting their taste and discernment, not something they have little control over like their ass.

Oh, and whatever you do, don’t “neg.” Everyone knows about it now, and it’s gross.

Ask questions.

A lot of these tips dovetail with our shyness tips, which is no accident — one of the biggest hurdles of flirting is just overcoming your reluctance and talking to someone you don’t know (or don’t know very well). And whether or not you want anything romantic with that person, asking a question is a great way to strike up a conversation. As long as your questions aren’t invasive, they’ll often make the question-ee feel good, too — as I’ve said before, almost everybody likes attention. Greene also suggests asking for help or advice, whether or not you actually need it. This tip is sometimes offered in an annoying, misogynist way in dating guides — “look helpless so he’ll want to take care of you!” But Greene suggests asking something like “which Chinese restaurant around here has the best hot and sour soup” — the goal isn’t to fake incompetence, but to make the other person feel smart and helpful, which feels good regardless of gender.

Make eye contact — but do it right.

Lena Chen of The Ch!cktionary told me,

The best flirting move for the non-confrontational flirt: a simple smile and eye contact. If your target hasn’t previously taken notice of you, this will pique their curiosity. And if they were already interested (or if they make eyes back), then this offers confirmation of mutual attraction. But just because you’re not approaching someone directly doesn’t mean that your less overt advances won’t make make them uncomfortable. You should be attentive to how your target is responding and not be a creepy person leering at uninterested parties from across the room. Also, it helps to remember that eye contact involves two pairs of eyes, not your eyes and someone else’s crotch.

Writer and speaker Gala Darling added,

The eyes have it. The very best way to let someone know you’re interested in them is to let them know you’re truly present, & maintaining eye contact is how you do that.

You don’t have to be all crazy-eyes, intensely staring into their soul or glaring at them. Just look into their eyes when they’re speaking to you. It’s best to do this with a hint of a smile, too, otherwise it can feel a bit Japanese horror film!

Touch — but again, do it right.

Both Chen and Darling recommend a little physical touching — if, that is, you already know the person you’re flirting with a little bit. Obviously, there are a lot of caveats here — even a pat on the shoulder can feel invasive to someone, and touching anyone in an environment where they might otherwise feel unsafe (ie. you’re strangers, alone together on a train) is a bad idea. Here’s when it might be more appropriate, according to Chen:

With a casual acquaintance, I’d recommend making subtle, but still friendly (i.e. not invasive), physical overtures (placing your hand on someone’s shoulder longer than necessary to make a point, picking something out of their hair, etc.) or suggesting spending time alone together (if this isn’t a typical feature of your friendship). That’s sometimes enough to send the message.

Darling says that with a friend you’d like to be more than friends with, “you can use physical touch to move things along, since there is already some familiarity established. Pair eye contact with a touch that lingers a few milliseconds longer than it needs to, add some laughter & you’ll have him or her eating out of the palm of your hand!”

And Sarah Croce of Autostraddle recommends “grazing her hips when you come up behind her at the bar put your hand gently on the small of her back” — again, definitely best if you’ve already been chatting or know each other.

Don’t be too subtle.

Writes Danger, “Subtlety is good, but not to the point where a girl has no idea you’re interested in her.” And as annoying as over-the-top flirtation can be, flying under the radar isn’t going to get you anywhere. Says Greene, “What prevents people from flirting is the fear of rejection, and when you don’t take control of your own social life you always feel, ‘what if?'” And while rejection does suck, especially at first, kicking yourself for not saying anything — and forever wondering what might have been — can feel even worse. So don’t be a creeper — but don’t just stare at your shoes and mumble about baseball scores either.

Much of the above applies online, too.

If you’re talking to people on a dating site, you can’t touch or make eye contact. But you can put a lot of the other above tips into practice. Says Darling,

Just act like you’re on a date: be friendly, ask questions, respond to what they’re saying, & be charming, cute, sarcastic… Whatever your personality is, let it shine! Move the conversation offline, too. You can only learn so much about a person from chatting online. Go on a date already!

Chen adds a few caveats:

1. Do not volunteer your measurements, or worse, offer a visual representation via email attachment.
2. Do not, I repeat, do NOT use the kissy face emoticon in conversation with someone you have not already kissed.

And there’s one more overarching tip stressed by everyone I talked to: do not use a pickup line. Unless, of course, you can top these.

Need help with a sticky social situation? Email us! We’ll sweep your social minefield!

For all Social Minefield columns, go here.

The Flirting Bible
How To Pick Up Chicks: A Lesbian Guide To Getting Girl-on-Girl Action [Autostraddle]
The Ch!cktionary [Official Site]
Gala Darling [Official Site]