8 New York Bartenders On Nailing The First Date

Photographed by Jess Nash.
When’s the last time you sat down for dinner on a first date? Yeah, we can’t remember either. Chances are, if you’re single and living in New York City, your calendar is chock-full of drinks with the Big Apple’s running list of bachelors and bachelorettes. So, how do we really nail those first dates? We turned to our secret weapon to learn the tricks of the trade: the city’s coolest bartenders.
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That’s right, bartenders aren't there just to serve up a gin and tonic on a moment’s notice. In fact, they’re actually your best wingman. They’re also there to take a read on any two people sidled up to the bar, whether it’s a sparks-flying type of encounter or a sky’s-falling kind of meeting (because we’ve all been there).
To get the inside scoop on tab etiquette, the telltale signs of a successful date, and where to go (and what to order) for the best romantic rendezvous of your life, we consulted the bartenders at some of the city's most beloved watering holes.
Not sure where to go? Choose a spot that’s nicer than your average Tuesday-night bar.
“[Pick] somewhere with a bit of class. I think you want warm lights, music that accommodates but doesn't overpower, conversation, and a sophisticated beverage selection — be it cocktails, spirits, wine, or beer. I also think it's considerate to choose a place that is convenient for the other person to get to.”
— Nathan Dumas, The Shanty
“[The perfect date bar is] kind of a blend of old and new: low lighting, candles on the bar, classic old woodwork. But, nowadays, the bar also needs to have a certain energy: not too in-your-face, but definitely feel-able. Oh, yeah, and clean. The bar you pick for a date says a lot about the environment you are accustomed to at home and in your everyday life. A sloppy, dirty bar means…well, you get the idea. And, pick one with no TVs! Your date is the reason you are there, not the game. The time to bond over sports is later.”
— Carlos Cruz, Sushi Samba
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“A place that has its music set just right will always make you feel comfortable, and possibly help you learn more about your date. And, a place that's not too crowded. No one wants to get to know you while they’re being elbowed by the happy-hour crowd.”
— Micaela Piccolo, Distilled
“[The bar] needs to be a place that’s conducive to conversation. You don’t want to go hoarse yelling at each other. Some places crank the music so loud, it makes communication challenging. Also, it should also be a place where both people feel comfortable. If your date is paleo, don’t take him or her to a beer bar.”
— Joaquin Simo, Pouring Ribbons
Or, pick a restaurant bar — ideal for an especially great date that can turn into a dinner.
“From my experience behind the counter, if one drink turns into dinner, you’re going to wake up the next day with coffee in hand.”
— Francesco Desideri, Florian Café, Trattoria, and Bar
If you’re nervous, chat up the bartender.
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“[One time], a girl was waiting at the bar, [looking] very nervous. I asked if she was okay, and she told me she was waiting for a date she met online. 'I’m not sure about this guy, but I’m going to give it a try,’ she said. I told her, ‘Well, if you’re not happy, give me a sign (she was going to touch her ear) and I’ll give you the check.’ After 20 minutes, she was totally fine.”
— Maxime Belfand, Saxon + Parole
“If your date is in the bathroom or arrives later than you, be friendly with your bartender; having someone on your team is always the right move. Part of a bartender’s job, in my opinion, is to act like a third party when appropriate. You can also always include the bartender in the conversation to kind of break the ice. It’s like having another friend there.”
— Jay Zimmerman, Sek’end Sun and Ba’sik
Put the cell phone away!
“When is a date going bad? When cell phones are being used. If you're on the phone a lot, we know you're not interested. Either that, or you are addicted to your phone, and that's a red flag for most people.”
— Micaela Piccolo, Distilled
Photographed by Jess Nash.
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Order what you like...but not too much!
“Drink what makes you feel comfortable, not what you think you'll be judged on. If your date is judging you because you're a guy and you ordered a Cosmo, or you're a girl and you're sipping Scotch, don't even bother for a second date. Anyone who's comfortable in their own skin will make sure you are drinking what makes you happiest.”
— Micaela Piccolo, Distilled
“Each person should order what they like. Suggestions between each other are a good way to start talking, but it is a bad start to insist your date should try something different. Unique cocktails are a great place to start, because it gives you something to discuss. Everyone has their favorite flavors, so just go with it and be comfortable. There's plenty of time to get adventurous on date number two."
— Carlos Cruz, Sushi Samba
“Drink whatever makes you happy. If you're getting a little fuzzy-headed and want to chill out, the first thing you should do is order some food. Then, maybe switch to something with a lower alcohol content. Collinses and highballs can help you slow down, as they are diluted with soda water and served over ice. Personally, if I'm getting to that state, I'll switch to beer, Fino sherry, or a nice Americano cocktail."
— Nathan Dumas, The Shanty
“Low ABV (alcohol-by-volume) cocktails are great; they have just enough alcohol to loosen you up, but not enough where you won't be in control of how drunk you get. Get a sherry cobbler, a Cynar and soda, or vermouth on the rocks. Have that and you can pace yourself; have one Zombie cocktail and you’re going to be wasted.”
— Joaquin Simo, Pouring Ribbons
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Your body language can say A LOT.
“You can see the way they look at each other, touch each other, and the way they drink. If one is reordering drinks while the other says no, things aren't going well."
— Maxime Belfand, Saxon + Parole
“Body language is key. Facing each other is good. Constant eye drifting and repeated trips to the bathroom signify a ‘How fast can I get out of here?’ state.”
— Carlos Cruz, Sushi Samba
“Things are usually going well when you see a lot of actual conversation; when someone is talking and the other person is actually listening. When it’s tough to get their attention because they’re so into each other, then you know it’s going well. Scanning the room while the other person is talking is, well, not so good."
— Joaquin Simo, Pouring Ribbons
“Good signs are: lots of smiling and laughing, being in their own little bubble, and not paying attention to the rest of the room. I do my best to stay away from some first dates, especially when they seem very involved in conversation. I do, however, pay close attention and make sure to jump in if they seem to run out of things to talk about. If they need a little ice-breaking, bartenders at Distilled are infamous for dropping tastes of the mead we carry in-house or a small taste of Champagne to celebrate whatever we feel needs celebrating."
— Micaela Piccolo, Distilled
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“What I see often is when one partner has a gin and tonic that’s halfway full, and orders another drink without asking their date if they would like something else as well. If I’m looking at the glass, I go directly to the date and ask, ‘What would you like?’ It’s just selfish and shows that they're not engaged in each other. ”
— Francesco Desideri, Florian
Photographed by Jess Nash.
Keep things light — it’s a date, not an interrogation.
“I once had a date going so well that I thought these two were destined to be. All of a sudden, she asked him about his planning for the future. Did he have a retirement plan? A 401K? What is he going to do to support his family if he has no plan? Blah, blah. Of course, I think these are all very important things to know about the person you could potentially end up with, but sometimes these conversations can wait until you get to know the person a bit more."
— Micaela Piccolo, Distilled
“In the United States, it seems that the conversation always starts with your job. That’s like a cold shower. Stop talking about jobs and reality, and start talking about your dreams.”
— Francesco Desideri, Florian
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Leave the exes out of it!
“Keep the conversation about previous dates and exes to a minimum. It happens a lot, actually; last week at my bar Bas'ik, this girl kept talking about her ex-boyfriend, but would always preempt it with, ‘Stop me if I’m saying too much, but this is what happened with him.’ If you have to keep saying that, you should not be talking about it. Her date was very cordial about it, and the evening didn’t seem to end poorly, but that sense of conversation is just very strange. Guys don’t like to compare themselves to other guys.”
— Jay Zimmerman, Sek’end Sun and Ba’sik
The easiest things you can do to make a date feel more comfortable:
“Ask each other lots of questions.”
— Nathan Dumas, The Shanty
“Be engaging, but when it's your time to listen, do so.”
— Carlos Cruz, Sushi Samba
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“Show up on time, smile, and let the evening unfold without expectation.”
— Micaela Piccolo, Distilled
Bartender-approved date spots in New York City:
“I like Attaboy because it always makes an impression on a date. It’s a speakeasy, so you ring the bell on a random door, and someone answers. It’s a beautiful space, very dark with great music. Sit at a table or the bar and order a great cocktail — it’s probably a spot that I would pick to go on a date. There is also Featherweight in Brooklyn. You want to bring your date to a place that’s a little classy, because it reflects on you.”
— Maxime Belfand, Saxon + Parole
L'Express is great for a late-night date spot, so if things are going well, you won't get kicked out!”
— Carlos Cruz, Sushi Samba
“Attaboy — it’s an incredibly great date bar; lively enough that it’s not boring or too romantic, so you can find dark corners and get to know someone pretty well. The drinks are incredible, and the experience is awesome. My buddy owns a bar in the East Village called Professor Thom’s, which just started doing Tinder Tuesdays — if you come in with a Tinder date and prove that you’re a match, you get two drinks for one. It's a hilarious idea and a great way to play off online dating. To be a bit fancier, I would go to the NoMad Bar. The restaurant is a little pricey, but the bar is a little dumbed-down while still being super-classy. And, the food’s awesome.”
— Jay Zimmerman, Sek’end Sun and Ba’sik
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Happiest Hour just opened up in the West Village and has become a personal favorite for its feel-good environment. In the same neighborhood, you'll find the romantic and deliciously executed Wallflower, which will swoon your guest. I also love hitting some hotel restaurants when meeting someone new. The Crosby Hotel has the best vibe for lunch dates and afternoon tea, while Isola at the Mondrian definitely manifests a whimsical experience with its decor and food.”
— Micaela Piccolo, Distilled
Raines Law Room, which is just great. If you’re stuck in Midtown, Lantern’s Keep is a great spot because it’s a little tucked away. Or, something like Dear Irving, which just opened. It’s a great spot with so much visual interest. Or, Temple Bar, which is an oldie but goodie. That place is just chock-full of dark nooks and crannies.”
— Joaquin Simo, Pouring Ribbons
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