Yes, we know—the apps suck, dating in New York is terrible, and there are versions of West Elm Caleb walking out of every bodega in Brooklyn. But when you miraculously sense a tiny glimmer of hope in a new connection, you should be prepared to see that through. Just be sure to keep in mind that while finding people to date may be a challenge, dating itself can (and should) be fun. I mean, would it kill you to bring a little jolt of romance back into your life?
A major key to making dating fun is choosing places you’d actually enjoy spending time in, rather than designing dates purely to impress a stranger. You want to find a way to share a great experience and let them know a little bit about yourself and what you like to do. And the spot you pick provides critical atmosphere for those precious and pivotal first moments.
Here are a few to consider for your next first date.
Bar Madonna
Address: 367 Metropolitan Ave.
When we think of a good cocktail bar, characteristics that come to mind include classy, refined, even sexy, but fun isn’t often considered or prioritized. Bar Madonna, the Italian-American-inspired cocktail bar in Williamsburg, is just that— it’s fun.
Named TimeOut New York’s “Best New Bar,” the cocktail menu is dynamic with drinks like a Limoncello Milk Punch and The Bialetti, a hazelnut-y espresso martini. The lighting is low and intimate, but the music ties it all together. Be prepared to hear a little In My Mind-era Pharrell and Juelz Santana’s “Hey Ma” regularly. And keep an eye out for more frequent DJ programming in 2025.
The room itself lends to plenty of conversation starters, as Bar Madonna extensively collaborated with KidSuper, who designed custom plateware for the tables and wallpaper within the bar’s restrooms, tagged his signature doodles to the team’s uniforms and a huge mural, which largely directed the vision for Bar Madonna.
And the best part: the kitchen is open late. A nod to pre-pandemic New York, Bar Madonna is a great pick for the only stop of the night, but it’s also the perfect spot to stretch the evening out a little longer when you find someone worth the time. Order the Smashed Meatball Parm sandwich and grilled artichokes to split, and loosen up a little bit.
Xanadu
Address: 262 Starr St.
There’s a page in the Dating App Bio Handbook that so many cis straight men have seemingly taken to heart. Something about wanting a partner that “doesn’t take themself too seriously,” which is kind of a red flag, if we’re honest. But for those who can laugh at themselves—especially after taking a tumble—Xanadu might just make for a properly unconventional venue for your next (last?) first date.
Xanadu is a rollerskating rink in Bushwick, but it’s not just any rollerskating rink. They have a 7,000-square-foot handpainted floor for skaters, and all the hallmarks of an old-school rink, from the incredible celestial-print carpeting to clearing the floor for a few songs for the advanced skaters to show out. There’s a full bar and concession, and in addition to DJs, they regularly have themed nights and live music. How much cuter could it get than rollerskating and holding hands on the first date? Do you want to go? Circle one: yes or yes.
Deux Chats
Address: 27 Broadway
The quintessential date spot, Deux Chats has the ambiance, the location and the menu. Just off the Marcy J-M-Z stop, it’s easy to meet someone coming in from the city to go out with you, but it’s also on a quieter, less obnoxious corner of Williamsburg. In addition to a menu full of small plates to share, their prix fixe menu ($45 for three plates) is a reasonably priced option to try a few things. Regarded for their martinis, they also have both spirit-forward and non-alcoholic options that are worth ordering and sipping on.
And the ambiance! Candlelight sets the mood. The tile mosaic behind the bar is beautiful. The gallery wall full of celeb portraits makes for easy ice-breakers without drawing too much attention away from the date, and the music is just the right volume for you to enjoy without struggling to hear each other.
Che
Address: 302 Malcolm X Blvd.
Sometimes you’re meeting up with someone and you aren’t quite sure if it’s a date. Other times a coffee and vibe check is more appropriate. Che lets you have that and affords you the opportunity for it to be more (but cross that bridge when you get to it).
On Tuesdays and Wednesdays, it’s a small cafe with coffees, teas, and what they call “day plates” served from 10 AM to 5 p.m. Thursday to Sunday evenings they stay open until 10 PM, serving a variety of natural wines and small plates, like fingerling potatoes and boquerones with ricotta. And the staff behind the bar is lovely and attuned to when to participate and when to sit back and watch you hit it off.
Kinjo
Address: 11 Adams St.
Japanese for “neighborhood,” Kinjo is a new addition to Dumbo that can truly support any type of date. From simple and low-stakes to full-blown omakase, this spot has range.
For something a bit more casual, post up at their beautiful bar or cozy up on the banquets aside it with something off their cocktail menu like a Shiso & Peach Highball or a Yuzu Negroni and their Snow Crab Dip or Mushroom Truffle Butter Rice Cakes. The house sake is also superb. It’s low-lit, the music is good (you might hear Portishead or the TikTok-popularized Snoh Alegra and Vince Staples track), and it’s very sexy without being pretentious or stuffy.
Or you can opt for the omakase and indulge, which is objectively better to do when there’s someone to get excited for every upcoming plate with.
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