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Bartender Confidential: Secrets to Bar Pickup Success

Picture of Kathryn Maier
NYC Food & Drink Editor
Updated: 12 July 2017
Even in an era when dating is dominated by Tinder, bar pickups are still a common way to meet people. And the bartenders see it all; they’ve learned what really works… and what really doesn’t. Here, a few of our New York City-based favorites offer advice on how to do it correctly.

People still meet the old-fashioned way: in bars. And no one witnesses more attempted pickups than bartenders. “It definitely still happens,” says Matt Friedlander, general manager at Sweetwater Social. “Sometimes it’s very successful and executed really well; sometimes it’s just a dumpster fire from the beginning.”

“I see it every night, and I still see everybody do it wrong,” says Zak Snyder, beverage director at Sons and Daughters of New York, located in the Meatpacking District, the epicenter of NYC’s singles scene. Bartenders have learned what works, and what causes someone to crash and burn.

In honor of the upcoming day of romance, we approached a few of our favorite friendly bartenders at some of NYC’s most popular spots for mingling to get their tips on how to successfully approach the hottie at the end of the bar.

Tip number one on the art of the bar pickup: “Don’t be drunk”
Tip number one on the art of the bar pickup: “Don’t be drunk” | © nd3000/Shutterstock

Let’s start with the number-one essential rule:

Do not approach anyone when you’re drunk

Each bartender I talked to told me nightmare stories about attempted bar pickups they’d witnessed. What each aggressor in every anecdote had in common is that every single one of them was very drunk. Don’t be that guy.

“The worst happens when somebody is drunk and somebody is not,” says Snyder. “The other night this guy came up to some women, and he’s very drunk and spilling beer everywhere, and in his head what he said to them was, ‘Hey baby, you’re beautiful, wanna dance?’ What they heard was, ‘Habrbfyrfhabuflmnefwq,’ and then he spilled beer on them.”

Point being, limit your pickup attempts to when you’re relatively sober: It’s in everyone’s best interests, including your own. “When you are massively inebriated is probably not the best time to try out pickups,” Snyder continues. “You never come off right when you’re slurring, and no matter how suave you think you are, most of the time, the bar staff is sober, and they’re watching you, and they are laughing.”

And now that we’ve gotten that out of the way, here are a few finer points.

Avoid cheesy pickup lines

“All of the lines are just terrible,” says Friedlander. “They’ve all been used. They’re dated. They’re cheesy.” He’s heard men attempt some of the classics: “You know what would look good on you? Me.” Or, “Is that a mirror in your pocket? Because I can see myself in your pants.” He advises, “Don’t do that. Just don’t use that line.” As Snyder says, “I’ve never seen any pickup line really work, and if it did, every woman I’ve talked to has said, ‘Boy, do I regret that interaction.’ ”

Instead, introduce yourself and have a conversation

Nice, natural conversation is a lot more sex-appealing
Nice, natural conversation is a lot more sex-appealing | © Joshua Resnick/Shutterstock

“Start off with, ‘Hi, my name is,’” advises Snyder. “A lot of people forget that. They don’t introduce themselves. They go up with a pickup line in mind, and they forget to introduce themselves. Look the person in the eye, don’t look them up and down, don’t eye them like a piece of meat. Just have a conversation.” This may seem obvious: Women are people; just treat them as such. But any woman will tell you that in a bar, people with decent conversation skills seem few and far between.

And after the introduction? The bartenders agree: Complimenting her drink order is a great conversation starter. “Some people take pride in what they order, or they have very specific tastes,” says Rafa García Febles, a bartender at Covina and The Roof at Park South.

And from there? Simply have a conversation. Put the best version of yourself out there. “Back in the day when I picked up people in bars,” says García Febles (he’s now married, so those days are behind him), “my successes were from finding a conversational in, and then just hitting it off from there and asking them questions, and follow-up questions, and details about what they’re telling you. Basically, as cheesy as it sounds, being a good listener is half of flirting, and half of conversations in general.”

It’s not rocket science. It’s just being a good conversationalist. García Febles continues: “I think just approaching somebody with respect and talking to them like they’re an actual person goes a long way in these situations,” he says. “Get good at talking to people. Get good at making people feel warm and fuzzy, and take it from there!”

Maybe send a drink

If the idea of going up and introducing yourself to someone terrifies you, think about sending a drink over, through the bartender, as an icebreaker. If the bar staff sense you’re a nice person with good intentions, they’re often happy to play wingman.

Sending a drink via the bartender is a great way to play it safe
Sending a drink via the bartender is a great way to play it safe

There are several benefits to this. First, the bartender acts as the go-between, reducing the stress of the approach. “I find that it’s the best icebreaker, because the bartender is a neutral ground,” says Snyder. Second, according to Snyder, offering a drink through the bartender has a higher success rate—about 40%—than walking up to someone and offering to buy them a drink when it’s more likely to be declined. And, finally, having the bartender as an intermediary gives the potential recipient of the drink the option of declining it less awkwardly than if she had to do so to your face.

A few things to keep in mind about this approach: First, the bartender should ask the other person whether she wants a drink. And be prepared to accept “no” as the answer. “I think it’s rude to just assume somebody wants something,” says Mellie Wiersma, a bartender at The Happiest Hour. “What if you’re done? What if you don’t want to get drunk?” If the drink is declined, don’t fight it. “The worst is if somebody rejects your drink,” says Snyder, “and you’re like, ‘No no no no, drink it.’ Why are you forcing a drink on someone? It’s creepy and weird.”

It’s your responsibility to time the offer right and send the correct thing
It’s your responsibility to time the offer right and send the correct thing

The general rule, according to Snyder, is that you tell the bartender you’d like to buy the person’s next drink, and after it’s delivered, the bartender asks the recipient if you may join them for the drink. “You make it, you drop it off, and then you say, ‘This gentleman over there sent it, and he would love to meet you. Is it okay if he comes over to talk to you?’ And they will either say yes or no, or ‘Thank you, but I’m busy,’ or ‘Thank you, but I’m leaving.’” In any case, says Snyder, “It’s the sender’s job and responsibility to understand that a yes is a yes and a no is a no, and that’s it.”

Also, it’s on you to time the offer right and send the correct thing. It’s poor form to send a drink when they’ve already got a half-full glass in front of them; double-fisting isn’t a good look on anyone, says Friedlander. “If the woman’s got a drink in her hand and you ask to buy her a drink, I’m gonna go, ‘You know, now’s not the right time,’ ” he says.

And it’s even worse to ask the bartender to send, say, a beer, when the person’s been drinking wine all night, or a Manhattan when they’ve only had gin and tonics. The best option is to have the bartender ask them what they’d like at the same time he asks whether they’ll accept your drink. And, bonus tip: If the recipient is with other people, buy the entire group a round. “Respect the situation, not just the person,” says Snyder. Not only is it the considerate thing to do, it may help turn the person’s friends in your favor, too.

Respect the social situation, not just the person
Respect the social situation, not just the person | © Olesia Bilkei/Shutterstock

And keep in mind: The drink is only an icebreaker. Your goal is not to get the target of your affections drunk. “A drink is an icebreaker. Your goal should not be to get someone drunk enough to have sex with you,” says Snyder. “That’s creepy! And rapey! And illegal!”

Also, by buying someone a drink, you are not buying their attention. “A lot of people seem to think it’s transactional,” says Garcia Febles. “It’s like, ‘I’m gonna buy you a drink and then you owe me a conversation, and if I keep buying you drinks there’s an expectation built in.’ Don’t do that. Somebody who receives a gift of a drink from a stranger doesn’t owe any conversation.”

As a counterpoint, some bartenders aren’t comfortable acting as a go-between, and some bars even have a policy against it. “I think it’s intrusive,” says Wiersma. “I don’t like it when I’m sent drinks. I don’t want to be sent drinks. But it’s awkward for me to say to a guest ‘I don’t feel comfortable doing that.’ ” But there are other ways your bartender can act as your wingman… if they like you.

Pay attention to body language

Check whether your target is looking at you
Check whether your target is looking at you

Still unsure about whether to approach? Read her body language. “A real surefire way of knowing if a woman’s interested in talking to you is if she’s looking at you,” says Garcia Febles. “If you catch her looking at you from across the bar, that’s a good sign that she might be interested, and at this point it’s up to you to just not blow it.”

Once you’ve approached, keep paying attention. “I’ve always advised friends of mine,” says Friedlander, “you start a conversation with someone, and you read their body language, the same way people do when they’re in a sales meeting, and you gauge how open and responsive someone is. And if they’re not, then cut your losses and move away.”

It’s pretty instinctive stuff, but just in case it’s helpful to have it spelled out: “It’s very clear. People who want to talk to you will let you know,” says García Febles. “They’ll make eye contact with you. They’ll kind of swivel their body on the bar stool so that their feet and their knees are pointing toward you. If you don’t get any of that, then it’s time to walk away. It’s not gonna happen.”

It bears repeating: Do not get drunk

“Sloppiness is never attractive,” Snyder reminds. García Febles concurs: “Being really drunk is not going to help you in any way,” he says. “When you’re stumbling and slurring when you try to introduce yourself to someone… Dude, no. Come on, man. Don’t be an amateur.”

Also: No physical contact

When asked about the worst scenarios they’ve seen, all agreed: Touching someone is crossing the line. “The biggest and most common mistake I see from behind a bar is that men have no sense of personal space,” says Snyder. Bad moves can range from a man physically squeezing himself between two women on bar stools and getting too close for comfort, to going up and starting to give a woman a back rub. “It’s just weird!” Snyder says. “You don’t do it on the subway. Don’t do it at a bar.”

García Febles adds: “No grabbing. If he sees it, he says, “We’re gonna switch from nice-host mode to headbutting them.”

Keep a polite distance and avoid any overtly physical moves
Keep a polite distance and avoid any overtly physical moves | © Zarya Maxim Alexandrovich/Shutterstock

Reject nicely, and accept rejection graciously

You’re not going to hit it off with everybody; that’s part of being human. “You may find out that you can’t stand each other!” Snyder exclaims. “You’ll be talking and you’ll be like, ‘Wow, this person is truly awful.’ You might say ‘Hi,’ and the person has a voice that makes your ears bleed.” In that case, he says, it’s best to just say, “Well, I have to get back to my group. It was great meeting you.”

García Febles echoed these words almost exactly, adding, “You’re probably not going to see this person again, so you can honestly be like, ‘Yeah, this is not gonna work. I don’t want to talk with you any more.’ ” It’s no big deal, he says. “Plenty of fish at the bar.”

Fewer rules apply if you’re a woman or a gay man

We’ve been addressing men hitting on women here, but most of the bartenders estimated it’s about 50-50 with women hitting on men. It’s just that, let’s be honest, straight men need a little more help going about it.

As one bartender put it, who asked not to have his name attached, “Gay guys are really good at hitting on each other; they don’t need my help. And women hit on guys all the time; usually the guys are just happy.”

When asked what he’d change about his advice if addressing a woman chatting up a man, Friedlander said, “Absolutely everything. I say to the girl just go for it.” It’s a little easier for a woman interested in a man, he says, because “Nine times out of 10, if a guy’s sitting at a bar and a girl walks up to him and starts chatting him up, he’s probably going to be interested.” Weirsma agrees: “Most of the time, I think men are happy for the attention.”

But the same basic ideas still apply. Don’t get drunk. Be respectful. Back off if your attention’s unwanted. “I find that women are a lot more intuitive,” Friedlander says. From what he’s seen, they know when not to approach someone, and they back down more quickly if they sense they’re not keeping a man’s attention.

Above all: Have fun

“Don’t take yourself so seriously!” says Snyder. “Order something fun. There’s literally nothing better than a man in a business suit walking up with a giant piña colada.” Have some jokes ready, he advises, or even a deck of cards. “If you’re having fun and you seem like a genuinely fun person, they’re going to respond to that,” he says.