First dates can either lead to a lifetime of sharing cereal with someone, or end after a single drink and an awkward conversation about how trees are kind of like large bushes. You never know how things will go - but if you want to give yourself the best chance of having a good time, it’s important to pick the right place.
Here are 23 of your best options. All of these spots are relatively casual (so it won’t look like you’re trying too hard), but they’re also impressive enough to make you seem like an adult person who’s capable of making good choices. A lot of them serve food, but you don’t necessarily have to eat a full meal at any of them, and they’re all perfect for either a 20-minute meet-and-greet or a three-hour date that could be optioned by the Hallmark Channel and turned into a rom-com.
Nitecap is small, and it gets busy. That might not immediately sound like the ideal combination, but sometimes when you’re going on a first date, you want a place where it’s a little loud and crowded. That way, any lulls in your conversation won’t seem too awkward, and you’ll be forced to sit close together in order to hear everything and avoid elbowing someone else (there’s a no-standing policy). And since this cocktail bar is in a little basement on the Lower East Side, it’ll be dark and at least semi-romantic even if you decide to meet up at 6pm on a Monday.
Even if “cool and casual” aren’t the exact words you think to yourself when picking out a first date spot, chances are that’s what you’re looking for. Dante has you covered on both fronts - it feels like a real Italian cafe in the middle of Greenwich Village, and if your date doesn’t go as well as you expected, you can at least drink an excellent negroni or three. There are also some small plates like octopus and burrata that are perfect to share, and the long bar is great for when you aren’t sure about committing to a table.
You know how you tend to like people more when you’re with them in an attractive space? No? That’s just us? Superficiality aside, Alameda is an excellent Greenpoint cocktail bar - it’s just a big bonus that it’s a beautiful as well. It’s hard for a date to go too wrong when you have a seat at the giant U-shaped bar, a perfectly-made cocktail in hand, and maybe a burger to split in front of you.
You never know when you’ll have to plan a date with someone who works in FiDi, or when your company will decide to relocate to a renovated shoe factory on Walker Street, so it’s important to be aware of several good date spots in Tribeca. Our favorite is Primo’s. It’s a semi-hidden cocktail lounge with colorful furniture and an Art Deco feel, and you can sit on a couch and have a great cocktail here. Your date probably doesn’t know about this place - but if they do, chances are they’re already a fan.
Every once in a while, something strange happens. You actually care (deeply) about how well a first date goes. If you’re currently experiencing this weird sensation, stop checking WebMD and book a table at 2nd Floor Bar & Essen. This bar is hidden above 2nd Ave Deli on the Upper East Side, and it’s a dark space full of little tables and red leather booths. The cocktails are excellent, and - while you don’t necessarily have to eat here - there’s some very good food like duck blintzes and pastrami deviled eggs. You also might hear one of John Mayer’s better songs on the stereo.
El Quinto Pino has two rooms to suit different kinds of first date needs - a bar where you can grab a glass of wine or sangria, and a dining room for more of a sit-down situation. The menu is made up of tapas, i.e. the ideal non-committal food. Nothing says “let’s take this slow” like a tiny plate of olives. If things look promising, you can move on to something more substantial (preferably the uni panini). Another huge plus? They take reservations.
Going out with someone whose passions include Japanese culture, craft cocktails, meticulous organization, and/or chicken wings? Then your first date soulmate venue is Bar Goto. It’s a really impressive operation, from the incredibly tasty drinks and Japanese-inspired small plates, to the cubbies for your personal items and the excellent table service. You’re not going to want to make your trip to Bar Goto a quick one, so we’d suggest coming here with someone you at least have some inkling you’ll actually enjoy.
After spending a full afternoon checking out this person’s online presence, you still aren’t sure if you’re going to want to pull the plug on this date after one drink. But that doesn’t mean you should go to a dive bar that smells like the inside of a shoe. If you’re on the UWS, try Vanguard Wine Bar. It’s a big room a few blocks north of Lincoln Center, and it has a long bar, plenty of tables, and some old-timey French decor. When you stop by, it’ll probably be full of a bunch of other people who are also trying to figure out if they’d rather be at home sleeping, and you can either have one quick glass of wine or hang out in a corner for a few hours.
Conversation starters (and/or savers) are a required element of any first date situation. And at Donna, there are many of them, like the beautiful design that makes it feel like a cocktail church, or the fact that this place has been open for four years and still no one seems to really know about it. But you could also spend an entire date talking about the drink menu itself, which involves a hieroglyphic representation of all the many cocktails available. We have yet to crack the symbols’ code - but if your date is going badly enough, you can just sit in silence concentrating until you figure it out.
Epistrophy is a Nolita neighborhood hang above all, but it’s also a great first date spot. You can go the drinks and appetizers route, or easily have a more filling Italian meal, and there’s outdoor seating for the warmer months. Grab a little table outside and split a bottle of wine, and/or stop by for Happy Hour when you don’t want to pay full-price for drinks with a relative stranger.
Aria is a dark little room that was basically made for a certain kind of first date. One where things escalate quickly. There’s plenty of wine, the food is good enough, and you definitely won’t be the only ones on a date here. This isn’t the first date spot for everyone, but if it’s the spot for you, congratulations.
Sure, you only just met, but you could maybe see yourself sharing a checking account with this person one day, and you don’t want to have to tell your kids that your first date was at a place where Toto was playing nonstop on the jukebox. So go to Blueprint in Park Slope, get a little booth with a marble table in the middle, and snack on some things like octopus and chicken liver toast. This is the nicest cocktail bar in the neighborhood (but it’s not ridiculously expensive), and it also has a back patio where you can try to locate the moon and offer it to someone.
Much like yourself, Crown Inn is charming, unpretentious, and it doesn’t look like it’s trying too hard. It’s the ideal spot for when you want to grab some drinks at a casual neighborhood bar that’s nicer than a dive, but not so nice that you’ll end up spending $20 per drink - and you can either grab a seat at the bar or hang out at one of the tables in the back. Think of this place as an above-average pub where you’ll want to be a regular, and be sure to hang out in the backyard when it’s nice out.
On a first date, you want a place that’s a little bit impressive. Not impressive in the way where you feel like you’re definitely underdressed, but in the way where you feel like, even if the date goes horribly wrong, at least you got to check out a cool spot. Eli’s Night Shift is such a place - particularly for the Upper East Side. It’s a cafe during the daytime, but at night it turns into a bar with good cocktails, and lots of food like pigs in a blanket, fish tacos, and a great burger.
If you’re looking for a spot where you can get a couple glasses of wine and some small things to share in Hell’s Kitchen, Casellula is one of your best options. This place is a “cheese and wine bar,” with an emphasis on the former - and with over 60 options, you at least know your conversation will last long enough to decide which ones to get. That said, if you come here with someone who doesn’t touch the stuff, there are other tasty things available too.
If you’re going on a date in Midtown, first off, congratulations for getting someone to go on a date with you in Midtown. Now comes the hard part of finding a bar that isn’t full of your coworkers or other people shouting at televisions. Try Bo Peep. The drinks here are on the pricier side, but the small basement space is full of vintage lamps and velvet furniture, and there’s live music courtesy of a pianist in the corner every night.
Lois is an East Village wine bar where all the wines are on tap and you drink out of tumblers. It’s a unique place, and, if your date hasn’t already been here, it’ll make you seem knowledgeable and possibly even cool. The space is also pretty attractive, with big round mirrors and plain white walls, but keep in mind that isn’t very large, and you might have to wait for a seat.
If steak tartare and whiskey drinks are things you both enjoy, Weather Up is where you want to be. This is a great cocktail bar with a very good first-date atmosphere, and it’s close to the Financial District, if that’s something you need to deal with.
When you walk into June, you immediately get the sense that you’ve already made the first (and possibly last) good decision of your night. The drink list consists of interesting, affordable wines and great cocktails, the menu is full of food that will do the job, and the service is good, too. There’s a big bar, some booth seating, and even a back patio covered in twinkly lights. Twinkly lights that will hopefully distract from any strange things you say about conspiracy theories or butterfly migrations.
That whole “impressive” thing we were talking about earlier? The Sisters space 100% qualifies - and not just in the typical cool-Brooklyn-hang type way. (Look at that pretty bar.) You could easily use it for a day date (the massive skylight is another great element here), or at night, when a DJ joins the party. The food is pretty good, but for a truly awesome two-step date you would do well to drink here while waiting for a table at Emily across the street.
Maison Premiere is still the best place for fancy drinks and oysters in Williamsburg, and maybe the entire city. If Williamsburg is an option, this is a tremendous first date move, partly because it’s fun, but also because the whole place feels like it was teleported in from the early 20th century.
There isn’t any signage outside of Dutch Kills. The entrance is just an unmarked door in the bottom of a small brick building that looks like it might be an abandoned garment factory, and when you effortlessly locate it, you’ll immediately seem impressive. Next, you can head inside the narrow, dimly-lit space and enjoy the best cocktails in the neighborhood. This LIC bar feels like a secret, upscale tavern, and you can get a semi-private booth and have a long, hopefully-intelligent conversation, or sit at the bar and drink something with a chunk of ice the size of a Rubik’s Cube. You’ll wind up spending a decent amount of money on drinks, but if you’re trying to seem cooler and more grown-up than you actually are, Dutch Kills is one of your best options.
Mr. Fong’s is right next to the Manhattan Bridge, and it isn’t too close to any subway station, so there’s a pretty good chance your date hasn’t been here yet. This is, of course, the perfect opportunity to be a hero and introduce your date to this wonderful neighborhood bar where you can drink a solid cocktail, listen to good music, and look around the room while you try to guess how long it took for each person to pick out an outfit. The space gets pretty dark and noisy on weekends, but if you stop by on a weeknight, you should be able to grab your own leather booth and maybe play something on the jukebox.