Where to spend Valentine's Day in NYC 💌

Whether you're single, married, or somewhere in between...

When I was in high school, there was only one place to eat on Valentine’s Day. That place was Max Brenner, which if you’re not familiar, was like if Willy Wonka’s chocolate factory was in Union Square. Couples went to share chocolate fondue and drink “choctails”. Groups of girls (I’ll never call it Galentine’s) ordered s’mores pizzas and left with chocolate syringes. Something about the grand dining room full of familiar faces, its warm scent of cacao beans roasting and those big, silly, sugary menus made us all feral for this restaurant. But the owner has since been dramatically pushed out and "banned from making chocolate" and I am not 15 years old anymore. My idea of a nice Valentine’s Day dinner has since shifted to something still fun, but sexier and way more savory.

The infamous s'mores pizza.

I've been single on Valentine's Day, in somewhat of a relationship but maybe not exactly in one, and certainly in one. Today’s column includes where I did and would eat again in all three of those situations. (There’s also a list of the best heart-shaped boxes of chocolate on the market, which is something I look forward to receiving every year.) We can start with that strange in between area. If you're in the early stages of something and don't know where it's going, I’d have a casual meal and a lot of wine at With Others or the newly opened Rude Mouth. I like that the latter’s bread and butter plate is a torn open baguette and pile of butter served on a crinkled piece of parchment paper. If you’re pretty sure it’s going somewhere good you can do what I once did in that situation and split a burger at Diner. It’s delicious, candlelit, fun — the waiters write the menu directly onto the table while they talk you through it — and like the other two spots, isn’t flooded with couples who make you uncomfortable.

Dinner at Diner.

If you’re in the late stages of a relationship and have an idea of where it’s going (and it's not somewhere good), maybe consider not going out to dinner on Valentine’s Day. If you must, you’ll want to go somewhere good enough to distract from what’s really going on but not so special that it will always be tainted if you do end up breaking up.