Here’s a hyper-specific request I get pretty often: What’s a good date spot near Union Square? I attribute its frequency to the many people in borough-gap relationships looking for a spot where their subway lines intersect. So this one goes out to all the couples — or singles on early dates — meeting in the middle.
And this time, rather than give you a bunch of suggestions for dinner, I’ve got a whole itinerary for one epic, multistop night (a format inspired by Rosie Peck, one of my favorite New York dining micro-influencers). So get your date night ’fit on and meet me under the climate countdown clock. How romantic!
Start with a drink in the most flattering lighting
I love Pete’s Tavern any time of year, but winter is when it literally shines. Pete’s claims to be the oldest continuously operating restaurant and bar in New York City, since 1864; there’s delightful history (it cosplayed as a flower shop during prohibition!), and most of the original features of the bar are still intact. As soon as November hits, they deck the place out with wreaths, Santa figurines and strands of red lights densely packed on the ceiling. Sit at the bar, drink a manhattan and beam at your date with built-in rose colored glasses.
Then, dinner somewhere cozy
Now that you have a flirty drink in you, it’s time for dinner. Nowhere is more romantic, especially in this neighborhood, than Casa Mono. This tapas restaurant has been open on the most charming corner, 17th Street and Irving Place, for more than 20 years, and it remains bustling, low-lit and consistently great. There’s really not a bad seat in the house, but if you love sitting at the bar there’s plenty of opportunity for you here. Order croquettes with aioli, razor clams a la plancha, and fideos — short, thin noodles made into a nest, tangled up with clams and chorizo, and toasted until the noodles get supremely crispy.
Then, some dessert
Caffè Panna is no hidden gem. In the summer, lines wrap around the block. And while it’s certainly not dead in the winter, it’s definitely more approachable, and the ice cream’s just as good. If you play your cards right, you can probably score two seats on the corner of the bar, the ideal place to share an affogato made with “Aud’s dream” ice cream (sweet cream vanilla with peanut butter swirl) and topped with super-thick fresh whipped cream. Or maybe get your own.
Backup option: a perfect black-and-white diner milkshake at Joe Junior, in a booth, two straws.
Or maybe a nightcap and a show?
Seems like everyone dating these days is looking for a jazz bar (not ideal for first dates, I know). Ideally, you’ll take your partner to one that takes reservations and has chic cocktails, like the new Midnight Blue from the owners of Martiny’s. They have three performances nightly, at 7 p.m., 8:45 p.m. and 10:15 p.m., and take reservations for both the bar and tables — either one a perfect place for you to crush a wasabi-laced sour or an old fashioned with your crush.
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