New York City’s best bartenders don’t have a lot of time off. But when they do get a chance to go out, they know the best bars, the best places to eat, and all the late-night spots. In VinePair’s Night Out series, we’ll be speaking with some of the top bartenders in the city to learn what they do when they aren’t at work. Consider this your guide to the perfect night out.

chaim dauermann from the Up & Up mixes a french air conditioner

Being a bartender is a little like being a cab driver. It’s one of the first things Chaim Dauermann, the head bartender at The Up & Up in the Greenwich Village neighborhood of Manhattan, tells me when I sit down with him. People simply need to stop dwelling on the negative when they order drinks.

“I don’t know if this is a cultural thing or a generational thing, but when someone asks, ‘What do you recommend?’ and I ask what they like, they’ll say, ‘Well, I don’t like tequila,’” Dauermann tells me. I quickly get the feeling that this is a common problem.

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“I’ll say, ‘O.K., but what do you like?’ And they’ll say ‘I don’t like anything sweet.’ And again, I’ll say, ‘But what do you like?’” Dauermann says. “So when I get to that point with someone where they just won’t respond, I say, ‘Look, pretend I’m a cab driver. When you get into a cab and they say where to, you don’t say, ‘Not the airport.’ You tell them where you want to go.”

From Dauermann’s perspective, his job is to make a drink that will get you where you want to go. He (and every other bartender) can’t do that if the person ordering the drink doesn’t give the right directions. So how does someone give the right directions? Get out of the cocktail mindset.

Think movies. Are you in the mood for a foreign film? Try a drink that’s a little deeper and more contemplative. More in tune with the vibe of a romantic comedy at the moment? A fresh tiki drink that goes down easy will do the trick.

“It’s about alleviating people’s anxiety and helping them feel free to reveal something about themselves to you very quickly,” Dauermann explains. “You have maybe 90 seconds to learn enough about them to make them happy.”

The tables at the up & up

Making people happy is something that Dauermann’s gotten very good at over his years as a bartender. He first got into cocktails and considered bartending as a possible future profession when he was 17. He was interested in drinking and interested in something that paid better than the minimum wage jobs he was working in Los Angeles. At 21, he lived in Humboldt County with an interest in spirits and a Mr. Boston’s Cocktail Guide.

“Picture me, 21, got my Mr. Boston’s guide and living in an unheated, crumbling Victorian mansion in the middle of a cow pasture in the middle of nowhere 300 miles north of San Francisco,” Dauermann says.

A lot has changed since then. In New York City, he’s worked in restaurants, dives, high-volume cocktail bars, depressingly low-volume cocktail bars, and everywhere in between except a rooftop. It’s given him a near-unparalleled inside view into the New York eating and drinking scene.

Where to eat

Ducks Eatery: A Texas barbecue and Vietnamese fusion restaurant in the East Village that’s comfort food in all the best ways.

L’Artusi: One of Dauermann’s favorite places, and where he recommends anyone visiting go to when they’re looking for Italian food.

Mamoun’s: A West Village staple for affordable falafel. Much of Dauermann’s eating happens between the train and the bar, and nothing beats a $3.50 falafel from Mamoun’s.

Where to drink

Chaim Dauermann pouring cognac

International Bar: A dive bar in the East Village that’s a movie-ready, always consistent dive bar.

The Roof at Park South: A rooftop bar that doesn’t skimp on the cocktail menu just because it can sell drinks on the view alone.

Seamstress: A cocktail bar and restaurant combo on the Upper East Side that delivers on both fronts.

Subject: Where you can have a beer, a beer and a shot, a bar snack, a spectacular cocktail, and play a game of pinball.

Suffolk Arms: An upscale cocktail bar with a casual vibe and good food.

Bar Goto: Japanese-inspired cocktails with an enticing ambiance.

Attaboy: Casual place to hang out in lower Manhattan that also serves up the perfect drink.

Slowly Shirley: The perfect place to continue the downtown vibe offered at The Up & Up located just a few blocks away.

What to drink at The Up & Up

the french air conditioner cocktail at the up & up

The French Air Conditioning: A cocktail with Pierre Ferrand Cognac and cinnamon. When Dauermann was in France visiting the Pierre Ferrand distillery, multiple Frenchmen told him that Americans are obsessed with two things: air conditioning and cinnamon. Dauermann understood the air conditioning comment, but not the cinnamon.

How else could Americans explain Big Red gum, Fireball, and the large number of cinnamon whiskies? No answer. So Dauermann made The French Air Conditioning as a tribute, and it’s been one of the best-sellers. Perhaps the French were on to something about Americans and cinnamon.