The best part of dating in New York is that the night does not end at 10. The worst part is that most people default to the same loud bar in the same loud neighborhood and then wonder why every late date feels the same. Here are five moves that actually use the city.
Walk the Manhattan Bridge from the Brooklyn side
Everyone walks the Brooklyn Bridge. The Manhattan Bridge is better at night. Start in Dumbo around the Time Out Market on Front Street, get a drink at Sugarcane on Front, then walk up to the pedestrian path entrance on Jay Street near Sands. The path runs alongside the B and Q tracks, so a train rattles past you every few minutes and the whole thing feels like a scene from a movie that has not been made yet. You come out at Canal and Forsyth, which puts you a short walk from a second drink at Forgetmenot or Bacaro. The full crossing takes about thirty-five minutes and works best if you have already had one drink and not three.
Late dinner at a place that respects the hour
A late dinner is a different animal from a regular dinner. The lights are lower, the staff is looser, and the conversation tends to go somewhere. Raoul's on Prince still seats people until close to midnight and the steak au poivre at the bar is one of the better late meals in Soho. Wo Hop on Mott in Chinatown is open until the early morning and is the right answer if you have been drinking and want salt. Cervo's on Canal does Portuguese small plates until 11 most nights and is small enough that you can sit at the bar without a reservation if you are willing to wait twenty minutes.
The rule for late dinner: order one more thing than you think you need. The leftover food is part of the date.
A real cocktail bar, treated seriously
New York has a deep bench of cocktail bars that get better the later you go. Attaboy on Eldridge does not take reservations and has no menu, so you tell the bartender what you like and they build something. Katana Kitten on Sixth Avenue in the West Village is loud earlier and calmer after 11. Double Chicken Please on Allen has a back room that requires a wait but is worth it if your date enjoys being slightly impressed. The Bar Room at the Beekman in the Financial District is the move if you want quiet and a room that looks like a set.
Go to one. Stay for two drinks. Do not bar-hop a cocktail bar.
Jazz, but the right kind
Smalls on West 10th is still the best late jazz move in the city. The cover is around 35 dollars, the room is genuinely small, and the late set usually starts around 10:30 and runs past 1. Mezzrow across the street is quieter and more for piano. Smoke up on Broadway and 105th is the Upper West Side equivalent and is underrated for a late date because the crowd is older and nobody is filming the band.
The key with jazz on a date is to pick a seat where you can talk between songs. Avoid the front table unless you both actually want to listen and not flirt.
The 24-hour diner, sincerely
A 2am diner stop in New York is not a fallback. It is the date. Veselka on Second Avenue at 9th is open all night and the pierogi are exactly as good as they need to be. Kellogg's Diner on Metropolitan in Williamsburg has been redone but still works as a post-bar landing spot. The Malibu Diner on 23rd in Chelsea is the move if you are coming out of a show or a downtown bar and want a booth and a milkshake.
Order coffee and one thing to share. The point is the booth and the hour, not the food.
A note on getting home
The late date in New York lives or dies on the exit. Decide before midnight whether you are sharing a cab or going separate directions on the train. Working it out at 2am on a corner in the cold is how good nights end badly. If you are unsure, walk them to their train. It is still the most romantic thing you can do in this city after dark.