How do you flirt with someone on the other side of a room?
April 6, 2011 8:45 AM   Subscribe

How do you flirt with someone on the other side of a room? Let's say I'm sitting in a bar at a table with some friends and I see a girl sitting with a female friend on the other side of the room who appears to look at me a couple of times. What should I do? Smile? Go over and say hello? Assume she was just looking in my general direction and not at me?
posted by rwatson to Human Relations (32 answers total) 21 users marked this as a favorite
Send her a drink with your compliments, would be the normal, non-creepy thing to do. If she's with a friend, you can make the decision to send them both a drink or send a shared bottle of wine so as not to offend the other party.
posted by DarlingBri at 8:50 AM on April 6, 2011

Go over to her and say hello! Talk to her. Ask if you may buy her a drink. If she brushes you off, walk away.
posted by palegirl at 8:54 AM on April 6, 2011

As a girl, strongly disagree with sending a drink without talking to her first, I'd personally find that creepy and unwanted (I bet I don't want what you just sent me, and now it's awkward, and I don't know if you're nice or what you want). If you would like to talk to someone, you go talk to them. No complicated stuff necessary.
posted by brainmouse at 9:00 AM on April 6, 2011 [8 favorites]

I think it is ok to send the bartender over to let the person know that you would like to buy them a drink, and ask if it is ok. Don't just send over a drink, though -you don't know if the person is on their way out, or some other reason doesn't want a drink.
posted by kellyblah at 9:16 AM on April 6, 2011

Unless you are living in the 1950s and a gangster I would NOT send a drink over.

Seriously who actually does that these days?
posted by mary8nne at 9:17 AM on April 6, 2011 [5 favorites]

After making eye contact once or twice across a crowded room, your next step is a prolonged mutual gaze. Let's say at least five seconds. Around second three, offer a tentative smile, which gets bigger as she smiles back. If this stage goes according to plan, she is probably interesting.

The next time she goes up to the bar, you go up too. Don't pounce on her, just casually happen to be ready for another drink at the same time she is. While you're waiting for your drinks, give her your pickup line. Nothing sleazy, obviously, just a no-pressure conversation starter.

If you can't think of a no-pressure conversation starter, you should not be picking up strangers in bars.
posted by milk white peacock at 9:18 AM on April 6, 2011 [9 favorites]

I mean "interested." No guarantees on whether she's interesting at this stage.
posted by milk white peacock at 9:19 AM on April 6, 2011 [2 favorites]

I personally find being sent a drink a lot better than having some random guy come over and force his company on me. I can refuse the drink or accept it, and I can express my gratitude directly or to the bartender, and I can ask the bartender to convey my message or ask the guy to come over - thus giving me loads of options and putting me in complete control.

The bartender is supposed to bring you one of whatever you're already drinking, so issue of possibly not liking the drink is moot (and truly, so what if you got something you didn't like? You're under no obligation to actually drink it!), and if you're on your way out you may reconsider and stay, or leave anyway and express your regrets - really, there's no better way to initiate contact at a bar in my opinion unless you're actually sitting next to each other.

Just because something is the old-fashioned way of doing things doesn't mean it's not still a very good way. Shows good manners and healthy respect, in my opinion.
posted by widdershins at 9:36 AM on April 6, 2011 [2 favorites]

In addition to being long paired off, I am pretty not-cool. So I might wave. Which I can assure you is so not cool enough for a lot of people, but they may as well know about me right away. Is your goal short-term or long term? Because if it's long term I'd suggest you want to do this in a way that reflect you, not all of us.
posted by phearlez at 9:51 AM on April 6, 2011 [4 favorites]

The bartender is supposed to bring you one of whatever you're already drinking, so issue of possibly not liking the drink is moot (and truly, so what if you got something you didn't like? You're under no obligation to actually drink it!), and if you're on your way out you may reconsider and stay, or leave anyway and express your regrets - really, there's no better way to initiate contact at a bar in my opinion unless you're actually sitting next to each other.

Yeah. Tell the bartender that you'd like to put that table's next round on your tab, if they'll accept. I think it's kinda classy and a no-pressure approach. One of three things could happen:

1) She accepts, and then takes the drink you just bought her and comes over to thank you, conversation started, and you go from there. Hooray!
2) She accepts, gives you a wave, you wave back, and that's it. Hopefully she wasn't drinking double Johnny Walker Blues.
3) She declines, gives you a wave (or not, even) and everyone goes on their merry way.
4) She accepts, gives you the hand signal for 'let's do it in the bathroom' and there you go.

The point is: nothing really even that awkward could come of this, let alone bad. I think it's in good taste and your not imposing yourself on her and her company. I mean, what if she's a married lady out for girls night? Buy the table a round and the worst that happens is that you probably flatter them a little, whether they accept or not. It's a nice gesture.
posted by Lutoslawski at 10:17 AM on April 6, 2011

No no no to sending over drinks of any sort to a girl you haven't first talked to first, or to a table with a girl and her friends whom you haven't talked to first. I hate this approach, every girl I know hates this approach, because it's FULL ON PRESSURE. Talking to a lady and gauging her interest and availability is so much better than simply macking on her from a distance with booze. This actually happened to me last month (I'm engaged but didn't have my ring yet) and I was super annoyed at being forced to do a horrible combination of #3 on Lutoslawski's list and slinking away after looking at the guy's humiliated face. Also, foreign drinks from unknown men creep me out for obvious reasons, so even if I were single I wouldn't drink it anyways.
posted by Hwaet at 10:26 AM on April 6, 2011 [2 favorites]

I am a female person, but my general approach would probably also work for a male person: Stand up and walk past her.
You asked not how to pick her up, or how to make her uncomfortable, or how to put the pressure on, but how to flirt with her. in the average bar, you've got 5 locations to work with: your table, her table, the bathroom, the bar, the door. Find a path that takes you somewhere near her half of the room, whether that means that you suddenly decide you need to talk to the bartender, step outside and make a phone call, or a trip to the restroom. Don't stare at her as you go, that's kinda creepy and implies you're coming over to talk to her. But glance her way. Does she look at you as you walk by? If there's any interest on the first pass, then smile and nod on your way back to the table.

Congratulations, you have flirted.
posted by aimedwander at 10:30 AM on April 6, 2011 [6 favorites]

Disclaimer: IANAPUA (I am not a pick-up artist)

I generally don't walk up to a girl hanging out with her friends without some sort of encouragement first. I worry about being that guy that my lady friends complain about and say things like, "I really didn't want to be a bitch, but he just wasn't taking any hints." I also know that when I'm nervous, I either am to self conscious to notice hints, or else I think that things like blinking, breathing and being composed of matter are all hints that she'd like me to go somewhere else and die.

So if I think a girl has possibly checked me out a couple times, I'll glance over in her direction every now and then. Eventually, eye contact happens. Hold it an extra beat, and give a friendly smile. If she's looking at you because she's interested/curious, she will reflexively return the smile before she even realizes. She might then turn away and blush, or drop her gaze and purse her lips to keep from smiling. Those are good signs. If she's actually trying to look past you at somebody/something else, you'll see instead an unconscious look of confusion or even annoyance. That's a stop sign. If she holds your gaze steadily and smiles back, she's unnervingly confident and self-possessed, and possibly a call girl.

If I get a go ahead smile, I like to get up and head over to the juke box with a couple dollars, and maybe try to initiate another smile-off on the way, because if she's really interested, there's a good chance she'll suddenly feel the urge to play a couple songs herself. This is like winning the indie kid lottery - you don't have to risk rejection by walking up to her, you have an obvious topic of conversation, and you can impress her with how not-trying-to-impress-her your music selections are.

If she doesn't wander over to the juke box, than wait until she goes over to the bar (if she's not sitting at it already) and try to strike up a conversation while waiting to be served.
posted by patnasty at 10:39 AM on April 6, 2011 [5 favorites]

Follow up: only patronize bars with juke boxes. This is just good advice in general.
posted by patnasty at 10:42 AM on April 6, 2011 [5 favorites]

I guess in the end it just depends on how touchy or whatever the girl you're trying to flirt with is. If she's prone to being creeped out by someone buying her a drink, you probably won't fare much better trying to chat her up out of the blue. So yeah, getting some sort of encouragement first either way, a smile, a gaze, something of that sort is probably a good idea no matter how you proceed.

On preview: What patnasty and aimedwander said.
posted by Lutoslawski at 10:43 AM on April 6, 2011

1) She accepts, and then takes the drink you just bought her and comes over to thank you, conversation started, and you go from there. Hooray!

This is why people like me are saying this is a terrible method. This is how to completely cop out of having to talk to a girl by having the bartender/waiter do it for you, and putting all the pressure/responsibility on the girl to then actually have to talk to you. And if she doesn't want to, she has to publicly and awkwardly turn down a gift instead of a "hi", again through a middleman to whom she probably doesn't want to have this conversation even if the answer is yes. Please don't do this.
posted by brainmouse at 10:44 AM on April 6, 2011 [1 favorite]

Please don't do this.

Ok, I take my advice back. The most convenient way to do it, then, so nobody has to talk to anyone or have any sort of conversation or engagement with another human being or take any kind of social or emotional risk is to do nothing, leave the bar, and put something on Missed Connections. You've inconvenienced no one, did nothing that may be misconstrued, and saved the money you may have spent buying someone a beer. True, you probably won't ever get to meet that girl, but at least you didn't offend, put out, or insult anyone by spending $4 on them.

Do we really live in a world where you can't buy someone a drink without any strings attached or questioning of intentions or awkward 'oh god' -ness? Stop this world I want to get off.
posted by Lutoslawski at 10:58 AM on April 6, 2011 [9 favorites]

There was an absolutely fantastic comment about a year ago regarding eye contact and gay hookups (ie. cruising). My search-fu is failing me here, but it seems that the advice would be applicable here.

Anybody remember that one?
posted by schmod at 10:59 AM on April 6, 2011

? Did you even read my post? I'm saying you SHOULD talk to a person. If you want to talk to someone, you talk to them. You be a grown-up. You don't cop-out by having someone else talk to them for you or by attempting to trick them into having to talk to you first, you walk up to them, and say "hi". Quest succeeded!

Do we really live in a world where a girl has to be OK with being pressured by someone who doesn't have the courage to initiate a conversation?
posted by brainmouse at 11:09 AM on April 6, 2011

Well, I get what you're saying brainmouse, but I guess I don't see it as a cop-out or ungrown-up, or whatever. It's an old tradition, and when I've been on the receiving end of this practice I guess I've never felt pressured or like I was being tricked or something, or even that the other person was lacking in courage. I just thought it was nice. I think it's sad to have such a grim view of humanity that a nice gesture must come with all of this baggage of trickery or immaturity or something. There is more than one way to say 'hello' if you know what I mean. Look, this isn't a practice I engage in frequently, but I've met some great people this way and I hope no one ever viewed the act as cowardly or sneaky or something. I was just trying to be nice and like, you're at a bar - so picking up someone's next drink? It's not like you're paying their electric bill anonymously, or something.

Look at it this way: what type of initiation do you feel comfortable with? What feels right to you? Do that, and then you're likely to meet someone who you are somewhat compatible with, right? For example, if I smiled at brainmouse and asked the bartender to put her next round on me, she would not be happy about that and then I'd know that that probably wasn't going anywhere (I'm sure you're wonderful, brainmouse, and I mean that sincerely, I'm just using our disagreement as an example to make a point). Don't go to hip hop club to try to pick up a cowboy, know what I'm sayin'?

I'm going to bow out now. I will reconsider my random acts of bar kindness before engaging in them next time.
posted by Lutoslawski at 11:26 AM on April 6, 2011 [1 favorite]

I think it's sad to have such a grim view of humanity that a nice gesture must come with all of this baggage of trickery or immaturity or something.

I think you'll find that the people who hold this view obtained it through unfortunately common negative experiences. Consider the possibility that their experiences are valid and that you are lucky to have thus far avoided them.

What type of initiation do I feel comfortable with? One where money and gifts don't change hands, thanks.
posted by milk white peacock at 11:31 AM on April 6, 2011 [2 favorites]

Lutoslawski - In days of more formalized miscegenation between the genders, just as men were taught to send a drink over to a woman they wished to talk to, women were taught to have the bartender or waiter simply thank the man for them if they wished not to speak, and inform the man that the woman would like the opportunity to thank him for the drink herself if she did wish to meet him. The woman didn't feel pressure because everybody understood the semiotics of the situation equally.

This is no longer the case with sending over a drink. Nowadays, most women don't know that it's ok to accept the drink and not have any more contact with him. They might feel obligated to go over herself, rather than simply inform the waiter that it was permissible for the man to approach her now. Also, back then, women were more constrained as to the non-verbal signals they could give off saying they wished to be approached, so this type of formalized query was just more necessary.

These days, the informality comes at the price of indeterminacy. On the one hand, you're left on your own trying to interpret a more subtle and perhaps vexing array of signals, but on the other hand, you also don't have to send a girl a drink just to get the very first signal if she's interested or not. Oh, and you're way more likely to end up making out with her in someone's doorway halfway down the block from the back.
posted by patnasty at 11:33 AM on April 6, 2011 [6 favorites]

Good heavens people, this is a bar, this is an uncomplicated situation. You can order her plates of beans until the cows come home.

Walk up and say "Hi, mind if I join you." The answer is yes or no, respond accordingly.
posted by tomswift at 11:38 AM on April 6, 2011 [1 favorite]

I tried sending a girl a drink once, about 20 years ago at the Brickskeller in DC, which serves hundreds of beers from around the world. I asked the waiter for a recommendation, and he suggested Old Thumper, so that's what I sent over. Unsuccessfully.
posted by kirkaracha at 11:48 AM on April 6, 2011 [1 favorite]

When your eyes meet, WINK!
If her response is in any way positive, stroll over and introduce yourself. Saves the cost of a drink, and winking is fun. I mean, really, think about it.
posted by pentagoet at 12:31 PM on April 6, 2011 [2 favorites]

I think patnasty has a good run down of the eye contact to smiling path that you want to go down before going over and saying hi.

That said, I am also (personally) open to being bought drinks.
posted by grapesaresour at 12:49 PM on April 6, 2011

I am going to vote against winking, but that is just a personal thing (though I've seen others react in the same way I do). There is something so...cheesy and weird about the wink (unless you are in your eighties, and then its retro and cute).

(sorry, pentagoet.)
posted by vivid postcard at 1:31 PM on April 6, 2011

I think my least successful attempts at "hello" are when I want her to carry the conversation. So if her reply to whatever I say is likely to be "yes, and?" I'm not giving her a chance to have a good conversation with me.

On drinks: I will buy a drink for a girl only if (1) she's my girlfriend or (2) I owe her one. If I was the kind of person who regularly gave out dollar bills to strangers, I might reconsider.
On the other hand, girls have bought me drinks before, and I'm fine with that!

2nd aimedwander's response for just getting comfortable. Eventually, though, you'll need to say something.
posted by jander03 at 2:07 PM on April 6, 2011

No problem, vivid. I happen to be cheesy and weird.
posted by pentagoet at 3:58 PM on April 6, 2011

Yes, first step is definitely to confirm that she is in fact looking at you. I have the habit of staring off into space when in thought and many a time I've been startled to see some fellow grinning back at me when my eyes came back into focus.
posted by abirdinthehand at 4:54 PM on April 6, 2011

First: Wait until she returns one of your glances with a smile while looking directly into your eyes (note: "glances", not "aggressive, hour-long stare"). If this doesn't work after repeated attempts, please, please just leave her alone.
Next step: Make a funny/weird face. If she returns it, it's good. If it makes her laugh, it's even better. If she gives you a annoyed/angry stare in return, or looks away, please leave her alone.

After several positive responses from her side, I think going over/sending her a drink/"accidentally" bumping into her at the bar and similar maneuvres are all OK and should not seem too off-putting or threatening.
posted by The Toad at 5:23 PM on April 6, 2011

If a woman really is repeatedly looking at you and returning your glances, especially if she is smiling or casting her eyes downward and has positioned her body towards your general direction, you are flirting with her and sending her a drink as the next step is not a horrible thing to do. I loved this approach when I was in this situation because then it legitimized me talking to them, if I wanted too. It is better than approaching the woman directly because if you have misinterpreted her actions she can refuse the drink or, even if she accepts it, she doesn't have to talk to you and does not have to deal with trying to make your unwanted attention go away. If she is interested she can go up to you and thank you and commence with verbal flirting and see where it goes from there. And getting someone a drink is a nice thing to do (assuming you expect absolutely nothing in return).

It is a bad idea to send a drink to a woman when she has not been looking at you; has maybe looked at you and then looked away; looked at you, did not smile and looked away; seems to keep looking at you but you are sat right in front of the door; seems otherwise engaged, or really isn't cluing you in to any interest at all.
posted by Polychrome at 4:22 AM on April 7, 2011

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