11's: One-Two Punch Dates in NYC
Where to go, and more importantly, where to go next
“I know a place.”
The ultimate test of whether your date is going well is if you can move things to a second location. Someone’s willingness to stick around for another round doesn’t tell you much about their interest level. But standing up, putting jackets on, and walking down the street to bar #2 — that’s how you know you’ve got something cooking.
But oh nelly! You used the Infatuation’s “Best First Date Sports In NYC” list, and now you’re in Williamsburg and your mind's gone blank about what’s nearby. You could roll the dice and just start walking, hoping you’ll stumble into a great scene (ballsy!). You could pull out your phone and fumble around searching for a bar with reviews over 4.4 stars, quickly scanning photos to ensure it’s got the right vibe.
But your best bet — the way to establish yourself as the confident, savvy king or queen you are — is having a sense for the next great move at all times. That means that even if I blindfolded you and dropped you at Bushwick Ave and McKibbin St, you’d know a well-crafted cocktail on a cozy couch at Otis is just blocks away.
Today’s 11s isn’t just another first date guide… We’re talking about where you should go — and crucially, where you should go next. The best one-two punches. From experience! Not ranked this time. Plenty of neighborhoods represented.
Want to be the person who always has a “move” in their back pocket? Consider upgrading your subscription and gaining access to Flood’s Worldwide and its Google Map. You’ll always have a hit within striking distance.
11's: One-Two Punch Dates in NYC
June into Congress Bar Cobble Hill, Brooklyn
A pair of bars without pretense. June is about as rock-solid as a date bar gets: Near the F/G, approachable, never too loud or chaotic, great back patio, bottles of wine are 20% off ‘til 7. As the night wears on, you’ll want to slide somewhere a little more intimate. Across the street, Congress Bar is tighter, dimmer, and a touch more lively. There are corner two-tops, lots of ledges, and a snug back room perfect for round 2.
Cherry on Top into Palmetto Bushwick, Brooklyn
This duo showcases the best of Bushwick. I recognize that’s not saying a lot. But eventually, even the proudest Manhattan dwellers will need a Bushwick hit — here it is. Start on the roof at Cherry on Top, drinking wine and playing cards (ideally gin rummy). Afterward, take a lil’ sunset stroll through Maria Hernandez. Then find some space at Palmetto, where the cocktails are good and the vibe is better.
Bar Belly into Parcelle Lower East Side, New York
Bar Belly, played out or not, remains a tremendous place for a date. It’s tastefully dim, there’s so much adjacent seating, solid service, good drinks, and free truffle parm popcorn. Your options from Orchard and Canal are truly unlimited. But a nightcap at Parcelle — a glass of chilled red on a curvy leather couch — is very hard to beat.
Bar Madonna into Mr. Melo Williamsburg, Brooklyn
This is a wildly good one-two, especially if you’re in cocktail mode. Bar Madonna is new, sophisticated, dimly lit, with beautiful double-height ceilings (plus, you can make a res if you like having peace of mind on a date). After, head to Mr. Melo with its curved nooks, excellent sound system, and incredibly friendly bartenders. It’s a relatively mellow bar (no pun intended) on weeknights, but gets vibrant — even a little dancey — on the weekends.
The Immigrant into Headless Widow East Village, New York
I’ve long said it: The Immigrant is the perfect first date bar. It’s a pretty standard place: no major design features, a simple, straightforward list of cocktails, wine, and beer, and a bartender who pretends to have never seen me before, even though he made me a Negroni earlier that week. Bars like this are important, because if the conversation sucks, there are no frills to mask the displeasure. A great cocktail on a shitty date only clouds your judgment. Solid is what you’re looking for. Headless Widow doesn’t have much more going on, but it is a touch moodier — candle-lit and lively. Perfect place for round 2.
Hartley’s into Doris Clinton Hill & Bed-Stuy, Brooklyn
The old saying goes: don’t take a date to your favorite bar because, god forbid, it gets tarnished by a bad encounter. I generally agree — but this combo is too good not to use. After a perfect pint in the cozy quarters of Hartley’s, you’ll depart a charming pocket of Clinton Hill for a barer stretch of Fulton. But what lies on the other side of your quick six-minute trek is Doris. Beyond the lemon-yellow door, the smell of incense and the glow of a spinning disco ball will get you right back in the mood. Save this one for at least a few dates in.
Café Lyria into Swift Noho, New York
An afternoon cortado into a creamy pint is, truthfully, as good as it gets. Lyria has a big time vibe going — it’s one of the few cafes I’d elect for a coffee date. There’s backgammon being played, people smoking cigs on the sidewalk, the music is intoxicating, the coffee is great (as is the matcha). If you decide your post-coffee move is a cold bev, sliding into Swift’s back room for a Guinness is a Flood’s supported maneuver.
Rhodora into Dick & Jane’s Fort Greene, Brooklyn
Rhodora is a place to go with someone you think you’re starting to really like. It’s a ‘figure out if you want to make this serious’ kinda place. Small, intimate, and a little rustic, the scene at Rhodora provides a great early indication that they’re someone to keep around. A few blocks down at Dick & Jane’s, under the red glow of the worn-in room, there’s a shoulder-to-shoudler closeness, and a hum that turns the mood up just enough.
St. Jardim into Katana Kitten West Village, New York
I don’t go out in the West Village often. Maybe this duo shows that. But I do love St. Jardim, especially around golden hour. Split a bottle of something crisp and orange and order some bread, butter, and cheese. After, see if there’s room at Katana Kitten, ideally downstairs. Katana Kitten is well-known and highly regarded, but doesn’t feel overly kitchsy. The energy is electric, and the sakura highball will have you feeling juiced. The contrast here — breezy coastal wine bar into lively Japanese cocktails — is a blast.
Bar Goto Niban into Sharlene’s Prospect Heights, Brooklyn
I’m a big Bar Goto fan. Their Lower East Side location is one of my favorite rooms in the city. Niban, their Brooklyn outpost, is a little less vibrant, but it’s still without question one of the best cocktail bars around. On the other side of Flatbush, Sharlene’s is where you should settle in for round 2 (and 3, and 4…). It’s a touch less gritty than a full-on dive, but still has the stickiness in the air that invites optimal High Life consumption — and allows for conversation to get a little less serious.
Bar Americano into Taqueria Ramirez Greenpoint, Brooklyn
Honestly, if you find someone down for this, they’re a winner in my book. Bar Americano is always busy but never overwhelmingly full. Find some ledge space and get to sipping on their house vermouth with orange foam, or a spritz of any kind. Once you’re riding a tasteful buzz, hop over to Ramirez before close for a few pastor tacos and a Topo Chico to bring you back to equilibrium. This should go without saying, not a first date move… But undeniably a litmus test for whether you’ve found a keeper.
Best one-two date you’ve been on? Worst? I want to hear about it. Drop a comment, let me know where you’ve been.
And for even more date options:
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