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7 Ways Your Bartender Can Be Your Wingwoman... If You Play It Cool

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Anthony Humphreys

A wingwoman beats a wingman any day -- let's face it, your boy might mean well, but his hat is on backwards. And while a willing wingwoman can be hard/impossible to find, there might be one waiting where you least expect: behind the bar.

No, female bartenders still don't want dudes to hit on them, but if you're a solid patron who doesn't give off the faintest whiff of van ownership, they might take it upon themselves to help you hit on someone else. The fact is, some bartenders like playing Cupid, as long as it's not Jeremy Piven's Cupid (Season 1 is on DVD; there was no Season 2). They see every expression of interest on every customer's face, and as with any good rom-com, they want to see what happens next. Helping "what happens next" happen is part entertainment, part power trip, and part good business.

We talked to Nora and Phoebe, owners/bartenders at New York's Lois, about how to get in good with your bartender, and what she might be able to for you once you do.

Bar stools
Anthony Humphreys

How to Get in Good

1. Before you try to befriend the bartender, befriend the bar
Favors are for the familiar. Go to the bar, ask the bartender her name, be friendly but not a creep, and leave a decent tip. Repeat. Only when she starts recognizing you as a regular more interested in the welfare of the bar than the welfare of your sex life will the wing-relationship develop. (Here's how to befriend the bar.)

2. Don’t forget to sit at the bar
Obviously! But still: leaning on the bar to order and then retreating elsewhere is a non-starter. Take a seat and get comfortable. Also, the bar is the bartender’s domain -- if you want her to use her power, you must be where the power is most concentrated.

Cell phone in pocket
Anthony Humphreys

3. Get off your cell phone
A cell phone in your face tells the world to leave you alone, in the same way that sweatpants tell the world you’ve given up. If a good bartender sees you drinking alone or with human friends, she’ll talk to you. If she sees you nose deep in stats proving Chris Paul's been the best point guard in history over the past five years, she probably won't.

4. Remember she’s at work
Getting drinks in hands is still her number one priority; no matter how eager she might be to help you break your dry spell/continue your hot streak, you're still going to have to be patient.

5. Communicate who it is you’re into
Bartenders might have a front row seat, but they don’t read minds. If someone at the bar is getting you all worked up (in a positive, romantisexual way), ask the bartender what she thinks about her. If you’re already on a date, wait for her to go the bathroom, then chat with your bartender about how it's going and maybe your bartender will help it go better.

Tray of cocktails
Anthony Humphreys

How Your Bartender Can Help You After the In-Good Thing Happens

1. She can ask you to carry something
Your bartender can feign being overwhelmed, and then ask you to help out by carrying a drink to someone’s table. This serves as a clear endorsement of your awesomeness (you're clearly an important person and the bartender trusts you), but it also makes you look as humbly helpful as a Boy Scout carrying a strange grandma’s groceries.

2. So she can manipulate patrons like pawns
Which could mean, say, asking a group of girls to slide down a stool closer to you to make room for another party, even if there is no other party.

3. She can tell you what someone's drinking
If you want to buy a woman a drink, you should buy her something she'll like (so, probably not a Bear Fight). Asking your bartender what the lady you’re after is drinking is a simple way to demonstrate, to both the bartender and said lady, that you’re both considerate and interested.

4. She can assess potential, and keep you from going down a dark path
According to Nora & Phoebe, this could mean telling you "No, that girl is not into you. I just heard her talking about her boyfriend," or "No you shouldn't be into that girl. I just heard her tell her friend that she faked a pregnancy to get back at her ex-boyfriend." Your bartender also has the scoop on all the regulars, which is nice.

Shot glass
Anthony Humphreys

5. She can keep you/her around until success happens
As our experts point out, it’s never hard to get a customer to stick around for a drink on the house. Giving one to you makes you stay in the game longer (it also doesn't hurt if a woman sees that the bartender likes you enough to give you a free drink); and giving one to the object of your attraction keeps her around long enough for you to work up some balls, son!

6. She can straight-up talk about you to your could-be
A straight-up, not-sleazy endorsement from another woman -- Wow, you guys really seem to have hit it off; he seems pretty great -- is invaluable, say Nora & Phoebe. "Sometimes ladies just need another lady to feel comfortable and also vet the situation."

7. She'll give you the reassurance of a soft landing
It's always helpful to know that, if you flame out horribly, there'll be at least one woman still willing to talk to you, and put out the flames with another delicious beverage.