NYC Bartenders’ Dos and Don’ts of Dating

The Up & Up
Katie Byrum at The Up & Up | Cole Saladino/Thrillist
Katie Byrum at The Up & Up | Cole Saladino/Thrillist

The spirit of Cupid, that meddling toddler made popular by 99-cent Valentine’s Day cards, lives on through NYC bartenders. Who is present for every single bar dalliance; privy to the romantic, to the profane, to the highs and lows of love? Bartenders. A friend of mine, in fact, was married by the very bartender who witnessed her relationship evolve from flirtatious drinking buddies to husband and wife.

Whether you’re on the prowl, or hitting the town with a longtime love, what makes for a better date night than grabbing a drink? Bars, pubs, speakeasies, breweries, taverns, lounges -- all pump blood through NYC’s dating scene. Finding a great bar is easy, but having the perfect drinks-date can devolve into a regular comedy of errors.

Bartenders see and hear it all. Whether your hope is for sparks to fly or to keep a flame alive, bartenders know the dos and don’ts of dating. Here is their advice on how to have a great night at the bar on your first date, last date, and every heart shake, ache, and break in between.

dutch kills
Dutch Kills | Cole Saladino/Thrillist

How not to screw up the first date from a damn dating app

Dating-app date data

Spotting a first app-date is like identifying tourists on the subway: they are the least comfortable people in eyeshot. App connections made manifest are distinct from say, a first date between kickball teammates, because the aspiring lovers are coming into this thing with little more than an avatar and a headline. That’s why Haley, a mixologist at Long Island City’s Dutch Kills, insists that you review your match a final time before your date. “Know who you’re meeting!” she says. “Nothing is more cringeworthy than watching someone try to discreetly scroll through their matches upon arrival to a date. Note their appearance AND NAME before you walk in.”

So what steps can you take to minimize awkwardness? “Do whatever you need to do to relax before the date,” says Nevada, a bartender at Double Windsor, a Windsor Terrace hub. “Whatever that means for you. Go to the gym, take two showers, rub one out if you need to.” One thing you should definitely do for an app date is avoid your local. “There might be people there you’ve flirted or hooked up with,” says Samantha, a bartender at Abilene in Carroll Gardens. “That’s gonna be distracting.” And, even if you think you have a high tolerance, you should try to keep your drinking pace aligned with your date’s. “When I see someone ‘lapping’ their date, it looks nervous and bad,” Samantha says.

“One thing I see all the time is people wearing costumes,” says Matty, a mixologist at Dutch Kills and downtown Manhattan’s Attaboy. “Don’t do that. Don’t wear an outfit that you don’t normally wear. Don’t posture. You look uncomfortable because you are.” Nevada implores women to choose sensible shoes: “Don’t wear heels you can’t walk drunk in,” she says.
Like all minimally decent people, Brooklyn Inn bartender Kevin disapproves of mansplaining, but it’s especially important to avoid on first dates. “Men need to shut up. I see it all the time and it’s the worst. You’ve presumably read this person’s profile. That should give you some cursory things to ask her about. Just listen to the person you’re with. Share with each other and you can power through awkwardness.”

And be ready with several possible exit strategies should things still go off the rails, Samantha says: “The worst is being stuck on the subway with someone after a bad date.” Ping a Lyft, pick a first date spot near a Citi Bike dock, or plan for a nice, long, head-clearing walk home.


How to score a one-night stand

Do’s and don’ts of doing it

You were gonna go home and watch Netflix anyway, why not add the and chill? The first step? “Leave the one-liners and pick-up lines at home,” says Matty. “They never work and they annoy everyone.” So with that out of the way, what should your approach be?

Kevin has deduced that, as opposed to laying down the realness, a sob-story, or unloading one’s insecurities, the shocking common factor in successful one night stands is, “the couples seem to really be having a good time. A lot of laughing and smiling.” Keep things light and have fun with it and you’ll be fine. Nevada encourages a straightforward, laidback tack that’s easy to bounce back from: “Make your pitch quick, easy, and casual. No pressure. Don’t give the hard sell. ‘No’ isn’t a point to be argued. If you’re cool about it, you come off as confident, and the person has a real chance to make an assessment.”

It’s also important to remember that just because the good times are flowing, that doesn’t mean the booze has to be. Kevin cautions against getting blackout schwasted. “If you’re not gonna remember [your one-night stand], what’s the point? Even a vague memory is better than nothing. At least there’ll be a story.” Plus, performance is a factor. “You certainly don’t want a reputation as a shitty lover. Alcohol can do that.”

As for the barroom makeout precursor to “wanna get outta here?” You may feel intimate under the dim lights, but you aren’t invisible, and sloppy, public PDAs are not a good look after the age of ever. “Don’t take up my bar’s real estate over empty glasses for an hour, just close the deal and go home,” says Kevin.

It’s also smart, since you are going home with a virtual stranger, to keep a nonjudgmental friend looped in. “It may feel weird for some people, but who cares,” says Barcade bartender Audrey. “Text them who you’re with and when you’re leaving.”

Courtesy of Abilene

How to have a date night as a couple

What a fun, sexy time for you

Lucky you, you’ve got a regular thing going. You’ve found someone who’s fun just to be around, and you don’t need to feel pressure to impress them with that hard to get reservation, insider nightlife knowledge, or cultural acumen. Now don’t let comfort curdle into complacency.

Date night isn’t just about maintenance -- it’s about having fun with your favorite person. “Go on an adventure!” says Nevada. “Go somewhere special. You live in NYC, not Iowa City or Tampa. Is Iowa City a real place?” But maybe you and your partner have a great local with a bartender you love. If so, Samantha suggests going there. “It feels comfortable and cozy, you can be free to be yourselves.”

Remember to keep things saucy. “Make a goddamn effort,” Samantha says. “Look good, like you did when you first started dating.” She cribs Dan Savage: “It’s a good idea to have sex before you go out to dinner and drinks, otherwise, you’ll be all full and tired and drunk afterward.”

So what to talk about when you’re actually out? “Avoid talking about work or telling old stories,” Nevada says. “And don’t talk about social media. In fact, turn your phones off. Don’t just put them away, turn them off. Engage, be a part of one another’s worlds. Don’t get distracted by your friends’ brunches or trips to Maui.” Without a doubt, keeping full attention on your partner is key to any date night’s success. “Couples I see who’ve been together for a really long time, they have genuine conversations, not ‘how was your day?’ stuff,” says Kevin.

And remember that if things feel a little stiff, you can always pick up a conversation with your bartender. They can be the X-factor you need to loosen an evening up. “It’s fun to get casual, tipsy, chat with the bartender,” says Samantha. “That adds a new element to things.”

Dutch Kills
Dutch Kills | Flickr/Nick Normal

How to have an affair

If you must

Nobody approves of cheating, a’ight? “It’s so, so lame,” says Nevada. “And it’s not even the cheating, it’s the lying and the dishonesty. I’ve seen lots of people take off their wedding ring before they hit on someone. Insanely uncool.”

It’s your relationship, your life, your choices, your reputation, and your responsibility. “It’s my job as a bartender not to judge,” Audrey says. Samantha agrees, “It’s certainly not my place to tell anyone what to do with their lives.” But that doesn’t mean they want to be implicated.

“Don’t get others involved in your bullshit,” Audrey says. Avoid any bar you may love or want to go back to. Don’t expect others to lie on your behalf. And don’t count on discretion if you yourself are indiscreet. “I’ve told people when [a married person is hitting on them] goes to the bathroom,” says Nevada. “‘Hey, FYI, that person’s married. Look up their Facebook if you don’t believe me.’ They’re grateful 100% of the time and I feel fine with it. Nobody deserves to be lied to.”

Do everyone a favor and take your show on the road. “Pick a different place every time,” says Samantha.

How to break up

I’ll take the tear and snot special, please

It ain’t pretty to break up in a bar, but as every bartender will tell you, it happens. “Bars are intimate, but they’re still public space,” says Audrey. That’s why her advice matches that from, Audrey, Kevin, Samantha, Matty, Haley and Nevada: don’t break up in a bar.

I’ve broken up with someone in a bar. It was unplanned, ugly, I regret it fully, and I’ve apologized profusely. And it left me with a lingering sense of duty to help palliate the experience of anyone caught in a bar for either end of a Dear John conversation.

If you’re the person doing the deed, save everyone time and energy, don’t wait, don’t draw things out, and don’t make any other plans. “Don’t plan a night out beyond whatever conversation you’ve got to have,” Samantha says. “You can’t expect to have fun after that.” Breaking up with someone after a night out is also a losing proposition. “It’s just not fair to build up someone’s expectations then drop a bomb on them.” She tells the story of a regular who asked whether he should break up with his girlfriend before or after spending an entire evening out together. “A lot of [patrons] ask my advice and I’m not always as free to be 100% honest as I would be with a friend.” But in this instance, the scenario presented was so deeply inconsiderate, Samantha felt obligated to lay down a harsh truth, tips be damned: “I was like, ‘that’s your night right there.’ Having plans [after breaking up] is just really lame and inconsiderate.”

The single biggest mistake anyone can make immediately following a breakup is trying to drown their sorrows. “Don’t try and drink it away and put your bartender in the position of taking care of you. Don’t make yourself someone else’s responsibility,” says Samantha. “Staying [in the bar after a breakup] is a mistake,” Audrey says. “Nothing is gonna solve your problem, especially not alcohol in that moment. Lingering and dumping your problems on the bartender isn’t a healthy way to cope.”


How to take yourself out on a date

We out here

Sometimes you just need to get out of your routine and you don’t want to be accountable to anyone but yourself -- that’s awesome and totally healthy. “I think people get self-conscious and assume someone’s watching them,” says Audrey. “The truth is nobody gives a shit what you do.” So go forth and don’t worry what anyone else thinks!

Savor the solitary experience. “Go somewhere that’s doing something interesting with cocktails,” says Nevada. “Pick someplace the bartenders are known to be friendly and inviting. Attaboy specializes in bespoke creations, so if you want a cocktail, you’re gonna have a fun little chat with the bartender and they’re gonna make you something just for you. It’s even part of their training to engage people drinking alone.”

Bring a book, a notebook -- anything that’ll absorb your mind -- and relax as you sip your drink. Just keep in mind that you probably won’t absorb much of what you read or detect your beverage’s subtler notes if the bar is three-people-deep. Save this for a weekday evening.

The other approach is to make a new friend. Forget Twitter; for stories and gossip, look to bar locals. “You could talk to anyone, have any conversation -- the night can end up in a very different place than you anticipated,” says Audrey. You’ve been warned.

Matty says that the bartender can be a kind of chit-chat matchmaker. “Engage the bartender in an open conversation and try to include the person you want to talk to. I’ve seen it happen and it works. Walking right up to people puts them on guard.” Just keep in mind that conversation, well-intentioned or not, isn’t always welcome.

“Nobody is entitled to anyone else’s attention -- alcohol degrades people’s sense of personal boundaries, and then you’re just invading someone’s space,” Kevin says. Reading people is key. Lookin’ at you, men. “One of the biggest issues women run into is not feeling like they can go have a drink by themselves,” says Nevada. “If a woman is reading a book or whatever, that’s not a cry of ‘come save me!’ Nope. It’s just me and my book, dude. Leave me alone.”

Nevada also insists that a night out with your phone isn’t a night out alone. “If you’re on social media you’re paying attention to everything but the super fun city you live in,” she says. “Put away your phone and pay attention to yourself.”

Suphachai Sinsuebphon/

How to win a date with the bartender 

They’re people too

There’s just something about being behind the bar that adds to a person’s mystique and confidence. “Bartending is inherently performative,” says Audrey. And, social though it may be, it’s still work. “Just because a bartender is being nice doesn’t mean they wanna fuck you,” says Samantha. “Us being nice is us being good at our job.” Potential suitors should keep the service aspect of the job in mind. “[Bartenders] are serving you, it’s inherently unequal. Don’t make [a bartender] feel obligated by holding tips hostage.”

“Of course there are occasions where someone comes in and you make a connection,” says Kevin with the caveat that, “we’re not expecting to go home with someone.”

In situations where you feel a real connection, patience is key. “If you really do have a crush on your bartender, become friends,” Nevada says. “Be cool and easy and ask questions. Maybe that’ll lead to you hanging out outside of the bar. That’s how my husband and I met.”

Bartenders “don’t have time to fuck around,” Audrey says. If you’ve decided you’re interested, use your words. Every customer I’ve ever been interested in has been respectful, tipped normally, ordered drinks confidently, was patient and generally aware of what was going on.”

Situational awareness and respect are bartender turn-ons. Bartender turn-offs? “Don’t be a creep and stare,” says Audrey. “I’m not into someone hanging out all night,” Kevin says. “They’re usually hammered by the end and I’ve got to count money and close up the bar.”

If you’ve got your mind made up, Haley suggests waiting until you’re done drinking, and making a friendly yet unambiguous move. “We talk to so many people each shift. I’m personally pretty clueless when someone’s hitting on me. A simple, ‘here’s my number, let me know if you’d like to get together sometime,’ before leaving is straightforward and respectful.”

“Most of this comes down to ‘know thyself,’” says Audrey. “The answer is not in the drinks you order, or the person on the stool next to you. Intention is important. If you’re going to a bar, know what you want. Are you trying to be romantic? Get to know someone? Fuck a rando? It’s kind of bullshit Zen, but it’s true: Set your intention and the rest should follow.”

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