A Rainy Day in New York (2019)

A Rainy Day in New York is a love letter to the city when it’s at its most romantic: slick sidewalks, glowing streetlights, and the feeling that anything can happen between one subway stop and the next. Woody Allen frames the weekend like a wistful jazz standard—light on its feet, full of amusing one-liners, and shot with the kind of charming cinematography that makes even bad weather look like an invitation. The performances keep it buoyant, with Selena Gomez bringing a grounded, quietly magnetic spark that turns a chance encounter into something you’ll want to lean in and listen to. It’s a bittersweet, old-school romantic comedy vibe—more mood and banter than big plot mechanics—so if you like your romance a little talky and your comedy gently rueful, this is an easy date-night pick.

A Rainy Day in New York is clearly aiming for a breezy, old-school romantic comedy where Manhattan feels like a glamorous playground and misadventures turn into fate. The problem is it often plays like a greatest-hits rerun: familiar setups, familiar quips, and a screenplay that leans on clichés instead of building characters you actually care about. If you’re hoping for sharp, modern wit or a story with real momentum, this can feel dated and oddly inconsequential, like it’s drifting until the credits roll. That said, the cast is game and the rainy-city atmosphere can be cozy, so if you’re already in the mood for lightweight, nostalgic banter, you might still find it pleasant enough.