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Gage & Tollner flaming dessert with the “let me tell you” badge
Photograph: Young Skeletons for Time Out New York | the flaming dessert at Gage & Tollner will set your hearts alight.

Let me tell you—There are plenty of ways to enjoy eating and drinking on Valentine’s Day in New York City

Whatever your infatuation saturation.

Amber Sutherland-Namako
Written by
Amber Sutherland-Namako

There is no lower-stakes holiday with as highly cherry-cordial-concentrated levels of divisiveness as Valentine’s Day. In the years before everything became branded as National Something Day, it was among society’s leading examples of Hallmark holidays. And even now, as those goofier fake fêtes abound, February 14, legit as it is by comparison, is still decried as “amateur night.” But in New York City, everything is amateur night, and nothing is. 

What might be one person’s Valentine’s extravaganza—or birthday, promotion, or anniversary celebration, for that matter—is another person’s Wednesday. In restaurants all around town, reservation occasions range from Big Night Out to nothing special, with myriad gradations in between. So the notion that any one date would suddenly assume a bizarro Purge-like quality, where the self-proclaimed dining pros are forced to lock themselves indoors, or otherwise encounter the teeming so-called amateurs salivating for the medium-rare myoglobin of prix fixe specials and the helium of heart-shaped balloons is simply unrealistic. 

Demanding schedules, forgetfulness and our signature nonchalance mean that plenty of New Yorkers will end up in restaurants this Valentine’s Day, regardless of intention intensity. And each tier of observer can have as romantic or disenchanted an evening as the commonly recognized illustration of their ventricles’ desires. 

For the “super-smitten”

Maybe you’re in a shiny new relationship, you’ve recently rekindled an old flame, or you’re just the sweetest little sweetie pie in town, you . . . probably already have a reservation at one of the best restaurants for Valentine’s Day dinner, actually. And, even if you don’t, who cares, you’re In Love!! But that increased heart rate can really work up an appetite, so, at press time, you can still book early dinners from that esteemed list, like Untable, late ones at Little Mad, and bookend slots at Cecchi’s.  

For the “casual fling”

Oh, you proximity cuties, you daring fly-by-nights, what better way to sharpen your exhilaration, your see you . . . next time? attitude, than high above it all, soaring on one of NYC’s most esteemed rooftops? “Too cold,” you cry? These winter-friendly locales are as covered as your true feelings. 

For the “comfortably in love”

Although there is some overlap here with the super-smitten, particularly depending on the day, the comfortably in love might have happily filed their novelty candy box, red rose bouquet and singing telegram days to the archives. If this isn’t an all-out year—they come and go—pop into your favorite dive bar and toast to not being Out There anymore. 

For the “couldn’t care less”

You mean business and this February 14 is a Business Night. Wednesday: Haveyouheardofit?? Since you’re blasé about the cardboard cupids anyway, you may as well leave room at destinations awash in that timely cherub aesthetic and stick to spots where it’s you-know-what as usual. I’m told that two personal favorite spots, Swoony’s in the Columbia Waterfront District and Sidney’s Five in the East Village will be up to their regular high standards this Valentine’s day, absent any mylar.

For the “actually-averse”

Just like I always say anywhere can be romantic—The Red Hook Ikea parking lot, the Staten Island Ferry, the elevated stretch of the 7 in Long Island City might all surprise you—almost anywhere can swing the other way, too. You’ll surely want to avoid those set menu spots, and while and a dive might seem like the mood, I’d stick to sports bars. Yes, sports are plenty romantic to many, I am aware there are even team-themed weddings, do not @me, but on this particular occasion, on this particular day, a nicely distanced game of skill and chance might be a welcome reminder that you don’t need a participation trophy. 

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