Some people swear by summer dating: good weather, better vibes and somehow drinking every night feels less socially irresponsible (and caloric lol) than in the winter. Fine, I get it — I’m more carefree in the summer, but the thought of sweating through my brand-new DÔEN dress while listening to my date talk about his “crypto side hustle” sounds legit mis.
And let’s be real: anyone actually worth dating is probably in the Hamptons, Nantucket or on some island in the south of Spain whose name I can’t pronounce.
Not all of us have unlimited PTO, so if you’re stuck in the city this summer and want to find your soulmate (or situationship), here are date spots that won’t make you pretend you “met somebody” and “want to see it through.”
City Vineyard
Nothing screams “good date spot” more than a glass of crisp white, a crowded sea of entitled Chase bankers in white linen and views of the ever-so-gorgeous Hudson River. Jokes aside, City Vineyard is a great place to bring Jessica from Hinge — the vibes are fun, it’s not super obvious and all girls are in better moods with wine in their hands.
Grand Banks
Grand Banks is a tough reservation, and yes, it’s on a (docked) boat — so I wouldn’t suggest it for a first or even second date. But three plus dates in, Grand Banks is a solid move: cool atmosphere, great oysters and strong drinks that make “I also matched with your sister” slightly less awkward. Plus, only serial killers (me lol) want to be stuck in a dark, crowded speakeasy in the middle of July.
Drift In
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This outdoor seafood spot is made for a first date — it’s super lowkey, but in a chic "I'm in the Caribbean" way. A cute location, casual energy and the crab dip might make her fall in love with you. If the banter is bantering, take a post-drinks stroll down the WSH (and hope you don’t see the girl you ghosted last week).
Dimes Square
Ask any of my friends — I’m a literal sl*t for Dimes Square. Between Le Dive, Parcelle and Kiki’s, this Lower East Side pocket gives Carrie Bradshaw energy… not La Caverna. It’s all petite outdoor tables, Negronis in every hand and men showing just a little too much chest hair. Sitting outside here is such a moment — chaotic in the best way — and honestly, it feels like you're in a rom-com.
Rooftop Cinema Club
An activity that involves no talking is obviously not a good first date. But after you’ve powered through the obligatory “where did you grow up?” and “what do you do?” small talk (as if you didn’t already stalk his LinkedIn), an outdoor movie is a fun, not-too-overdone option. Rooftop Cinema Club says, “Let’s hold hands while watching How to Lose a Guy in 10 Days”… but in this climate? You probably will.
The Skyline Drive-In
If you’re after something a little more intimate, Brooklyn’s Skyline Drive-In is a vibe. The one catch: to get the full experience, you’ll need a car (and, obviously, a bag of Lesser Evil Himalayan Salt popcorn and Hu dark chocolate). Not the most accessible option, but if you pull up in a BMW, she might start browsing rings mid-credits.
Brooklyn Crab
This Red Hook seafood shack is giving East Coast summer — same quality food and energy, minus the purple hydrangeas and Duryea’s lobster cob ruining your feed. Before schlepping to Brooklyn, make sure your date actually likes seafood. If they say they’re “scared”... you should be scared of them.
L'Industrie/Fini Pizza
A random $3 slice shop is def not a girl’s dream date — but L’Industrie and Fini are not the same as your local pizza joint and very much written in different fonts. Split a few slices — the famous white slice with lemon or fig jam, bacon and goat cheese — then wander around Brooklyn talking about the Williamsburg brownstone you’ll never actually buy.
Softside
I highly advise not taking Brooke Hinge to 16 Handles or Tasti D-Lite, but Softside fits into the same category as L’Industrie and Fini. If you’re not ordering the vanilla with olive oil and sea salt, you don’t deserve a second date. But if you are, split one with two spoons and stroll through SoHo while she pretends to care about your investment banking job.
Chinatown
Delicious food, built-in convo starters and just cultured enough that she’ll believe you actually enjoy going to the Met. Joe’s, Nom Wah and Spicy Village are top picks — but if the wait’s ridiculously long, there are a million other solid options within a few blocks. I can’t think of anything worse than waiting on line listening to your date talk about their love of space.
Central Park
It might seem a little cheesy, but a picnic in Central Park is a super cute date idea. Obviously, food and drink are non-negotiables — bring a spicy scallop roll from Sushi Seki and that bottle of wine she mentioned in her profile. If you're nearing the exclusive stage, it's the perfect place to post a cryptic photo of her arm… the softest of soft launches.
The Roof
Before you think you can take her up to your roof, hit a J for five minutes, and then casually ask if she wants to “go outside." Let me be clear. A roof date is only acceptable if it includes wine or spritzes (figure out if she’s a Hugo or Aperol girl beforehand), crispy rice from Kotobuki and your best Apple Music playlist. Do whatever you want after, but if you're planning this date just to hook up, don’t. She's not stupid, and it’s giving lazy.
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