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Eleven Rules of Barroom Courtship

There is no one more qualified than a bartender, with his front-row seat to primal New York mating rituals, to lay out the dos and don’ts.

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Illustration by Peter Oumanski  

1. Don’t have the bartender do your dirty work.
“The No. 1 thing you can do to turn a girl off is buy her a drink. It never works. I have never seen ‘Hey, bartender, do me a favor, buy these two girls over there whatever they want’ be successful. It’s usually accompanied by a creepy lean-in and an awkward wave.”—Dan Sabo, bartender at Five Leaves, Nights and Weekends

2. Don’t spill your drink on someone.
“Lesbian dating is probably a little different than straight dating; girls are less threatened by other girls, and some can be really aggressive, even a little scary. I once watched someone purposely spill a drink on somebody else—she just dumped it on her. The spilled-on woman was not into it.”—Danielle Badke, the Dalloway

3. Play it cool.
“Say you’re sitting at the bar and two girls are talking. Try to enter into their conversation casually. Just look over your shoulder and be like, ‘Oh, my cousin went to Pratt.’ That’s the better way to go than just being like, ‘Can I buy you a drink?’ ”—Drew Moore, Tutu’s

4. Go at 7:30 p.m. on a weekend to meet your future spouse.
“If you’re gonna try to meet someone, do it before 11 p.m. After eleven, that’s not long-term material; no one is looking for a serious relationship. 7:30 p.m. is when you’ll have good conversation.”—Sabo

5. Go at 1:30 a.m. on a Monday for a one-night stand.
“As opposed to a Friday, it’s a nonthreatening night. People don’t seem like they’re out trying to meet people … but they are.” —Caralyn Stone, Boat

6. Perseverance pays off.
“There are certain women we call ‘the Dalloway Stalkers.’ They aren’t interested in anything serious, but they’ve been here enough, they know what nights and times to come to find single women—usually Tuesdays—and they do really well for themselves.” —Badke

7. Be a jobless guy in Greenpoint.
“It’s a good time to be a young musician without a day job. If you have a great collection of flannel, you’re a little bit scruffy, you have a skateboard and maybe a shitty old hat, just post up at the bar and put out a vibe, and it’ll happen. Girls here are on the prowl. And the women have cool jobs, they dress well, they don’t get wasted every night. It’s a real problem: There’s a shortage of good men.”—Sabo

8. Keep it classy.
“It’s funny watching people come in on their best behavior, start out drinking slowly, and by the end of the night, they’re hammered. Too much alcohol brings out the worst in people when they’re on a date; it’s not a good look when they get so drunk they’re basically dry-humping at the bar. Keep an element of mystery.”—Amanda Vazquez, Village Pourhouse

9. Don’t be desperate to impress.
“People sometimes go into dates being like, ‘I gotta make sure they know I did X, Y, and Z so I seem worldly and cultured.’ The other night I’m at my station making a cocktail and this guy interrupts the girl he’s on a date with and asks me: ‘Is that sage?’ I was like, ‘What? Yeah,’ and he goes, ‘When I was traveling through Asia, I taught people how to plant sage. I learned a lot about horticulture, and Asia.’ He obviously was waiting the whole night to tell her this story. I saw her eyes just glaze over, and I thought to myself, That was it, that was your big moment—and you bombed.”—Sabo

10. Don’t be a sleaze.
“Coming up behind girls and randomly dancing on them—that’s just not okay.”—Vazquez

11. Don’t act buddy-buddy with the bartender.
“A lot of guys who’ve come in like three times will be all, ‘Oh, I know Caralyn.’ If they’re with a girl, they think they’re so cool because they know the bartender. It’s like, ‘No, I don’t know you, we’re not friends, and I’m not about to vouch for you.’ ”—Stone


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