A Low-Key Night on the Upper West Side With Pasta & Wine

Start your night off over pasta and paninis at Piccolo Cafe. This rustic Italian eatery makes up in flavor what it falls short on in space (it honestly feels like it was airlifted straight off an Italian promenade). Subway tile and old Italian newspaper clippings line the walls, and if the smell of Italian spices wafting out of the kitchen doesn’t pull you in, their wine list ought to do the trick.

Next, head over to Lilly's Cocktail and Wine for a nightcap and environment that's sure to set you both at ease. We love this exposed brick wine bar for their large selection of wines at affordable prices. They get busy at night, so be sure to get there early enough to snag a table. This place lends itself perfectly to intimate conversations, not the kind of wine bar where you're screaming to hear each other.