The One-Two Punch Guide: Winter Edition

How to plan a two-part date when it’s 10 degrees outside.
The One-Two Punch Guide: Winter Edition image

photo credit: Noah Devereaux

Dinner and drinks is a classic date-night combination, and that’s exactly why we made The One-Two Punch. It’s a guide with a bunch of dinner/drink combos that’ll help you plan a good date with minimal effort.

Unfortunately, NYC gets cold in the winter, and a 10-minute walk from a bar to restaurant can feel like a 30-minute trip across the surface of a planet that technically isn’t habitable. Which is why we made this Winter Edition. It has a bunch of restaurants and bars that are less than one block apart, so you can plan a date that’ll actually happen.

The One-Two Punches


West Village

$$$$Perfect For:First/Early in the Game Dates
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The West Village has so many bars and restaurants that we sometimes forget about Wallflower. It’s still there, however, and it’s a good low-key spot for a couple of drinks with someone who shares your interest in dogs, cloud formations, the Japanese art of ikebana, or none of the above. It’s a small place, with a little bar area up front, and it’s charming in a typical West Village sort of way. They also serve a full dinner menu with some small plates, in case you get hungry before your next stop.

photo credit: Noah Devereaux

$$$$Perfect For:Date NightSee And Be Seen

Exit Wallflower, take a left, and you’ll see Don Angie at the end of the block. It’s one of our favorite Italian places in the city, and it’s where you should grab dinner after a drink or two at Wallflower. Just be sure to make a reservation if you don’t want to be stuck outside, shivering as you stare through the front windows and watch other other people eat the lasagna for two (which is actually more like a lasagna for four).

Bring someone to Emily, and you’re already doing better than 99% of the people that your date has dated. This is the best restaurant in Clinton Hill, and they do two things very well: pizza and burgers. Sure, the burger might cost $27, but it’s also one of the best burgers in the city, which means that it’s priceless - like a family heirloom or a text from your ex saying something like, “I was wrong, and I miss you so much.”

After Emily, there are a few places in the area where you could grab a drink, but we can say, in all honesty, that none of them are closer than Hanson Dry. So if it’s freezing outside and you’re afraid that your date will secretly resent you if you suggest an after-dinner bar that’s more than 50 feet away, this is where you should go. It’s an unpretentious cocktail bar, and if you find a quiet corner, it’ll even feel somewhat romantic.

The dining room at Kings County Imperial is dark and intimate, and it’s a perfect place to hang in the winter. It also happens to be our favorite Chinese spot in Williamsburg, so you should come here with a date and eat some dumplings with their homemade soy sauce.

Union Pool is just around the corner from Kings County Imperial, and it’s the sort of place where you and your date will probably have a few drinks then get weirdly honest about your previous relationships. This place is lively and spacious, and it tends to get loud, busy, and filled with people who are secretly afraid of being alone and address this fear by taking shots of tequila and talking to strangers. In other words, it’s fun.

There are certain things you look for in a date-night bar, and Good Night Sonny checks off most of these boxes. It has good food, great cocktails, it usually isn’t impossible to find a seat, and it’s in a location that most people won’t have a problem getting to (the East Village). We also like the fact that it’s cooler than your average bar, but it’s still casual enough that you can just stop in for a quick beer.

If you’re planning a date in or around Clinton Hill, Aita will never not be a good option. It’s a neighborhood Italian place decorated like an English professor’s weekend home in the Catskills, and it’ll make you seem like a mature, thoughtful person who files their taxes on time. You should also know that the food here is great, and, while the pasta portions tend to be a little small, you probably don’t shouldn’t eat to capacity on an early-in-the-game date anyway.

The Mayflower


In any season other than winter, drinks at Mayflower after a dinner at Aita would seem like a lazy move. But if it’s anywhere south of 40 degrees outside, your date will appreciate the fact this cocktail bar is just next door. It’s also from the same owners, and it’s similarly quaint in an antique-store kind of way.

photo credit: Noah Devereaux



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Leuca is big and impressive, and you can bring just about anyone here. If you spend time in Williamsburg, it’s a useful place to know about, and it works perfectly as a last-minute date-night option when you need something that feels like it’s hard to get into. The food is slightly-fancy Italian, with things like pizza, pasta, chicken and tuna crudo, but it’s casual enough that you can wear jeans and sneakers.

Leuca is in the bottom of a hotel, and, at the top of this hotel (the William Vale), there’s a bar called Westlight. This means that you can have a two-part date night without ever going outside. Just head to the lobby after dinner, get in an elevator, and press the giant button that says Westlight. You should, however, be sure to make a reservation if you don’t want to run the risk of not getting a seat.

Sometimes, it’s nice to look like you aren’t trying too hard. If you do this correctly, you can convince someone that you’re cooler than you actually are. So for your next date night around Bed-Stuy, start at Glorietta Baldy. It’s a low-key neighborhood bar, and it’s almost definitely cooler than wherever you hang out with friends in your own neighborhood. Stop by with your date, grab some stools, and have a few cocktails while you figure out how much you like each other.

If it’s winter, and you’re drinking at Glorietta Baldy, your next stop should be Hart’s. It’s just next door, and it’s one of our favorite restaurants in Brooklyn. This place is small and romantic, and it’s an ideal spot for a dinner with someone that you could see yourself owning dogs with. The Mediterranean/American food is also excellent, and you don’t necessarily need to spend a fortune here. (The burger is both great and filling.)

Via Carota doesn’t take reservations, and there are ocassionally waits of up to two hours. Fortunately, we just informed you of this - so now you can just come early and put your name in. Once you do that (and the host writes your name in chalk on a big metal pole), you can go grab a drink somewhere else. This place is just one room in the West Village with floor-to-ceiling windows and a bunch of two-person tables, and your date will probably think it’s either cute, quaint, or both of these things. It also gets bonus points for having plenty of vegetarian options, and the pastas are reliably top-notch.

After you put your name in Via Carota, head to Marie’s Crisis. It’s a little, divey bar in a basement just a few feet away, and, inside, there will always be a pianist there playing show tunes. That’s what you come here for, and everyone is encouraged to sing along. Even if you don’t consider yourself a Broadway nerd, however, you’re bound to know at least one song, and your date will be impressed that you know of such a place where Christmas lights are up year-round, and half the people seem to know one another.

Esperanto isn’t new or upscale, but it’s fun and casual, and they do pitchers of cocktails. Will you order a pitcher of caipirinhas to share over dinner? Probably not. But at least it’s an option, and you could save a little money by ordering in bulk. For dinner, you’ll find mostly-Brazilian things like chicken with adobo, salmon, and seafood stew, although there’s also a burger if you prefer eating with your hands. The space itself feels sort of like tropical-themed home, and it’s casual in way that, if you weren’t on a date, you could wear sweatpants.

photo credit: Team Infatuation

$$$$Perfect For:Date Night

If you want something a little fancier after Esperanto, try Mace. It’s a little bar a few doors down where they take their drinks very seriously. The cocktails here have ingredients like rooibos, masala, and wasabi salt - and this should provide topics for conversation if you’re on a first date and have already discussed such things as siblings, college majors, and your dreams from the previous night. This bar also isn’t as pretentious as it sounds, and, most importantly, it’ll take you less than thirty seconds to get here from Esperanto.

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Suggested Reading

Leuca image


Leuca is an Italian restaurant with Manhattan vibes, in the bottom of a Williamsburg hotel called The William Vale.

Esperanto image

A local Infatuation mainstay, Esperanto’s got that little something special that that’s kept it in heavy rotation.

Kings County Imperial image

Kings County Imperial serves Chinese food in Williamsburg.

13 Spots Perfect For A Blind Date image

Where to take someone you don’t know (and maybe met on Tinder).

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