The problem with "things to do with your boyfriend in NYC" is that the standard list — dinner, drinks, walk — is the same in every city. NYC has options that are specific to the city, that boyfriends will actually remember six months later, that don't feel like a repeat of last Friday.
The memorable ones
1. A sightseeing flight over Manhattan
The most-remembered date NYC offers. Azzurra City Tours runs sightseeing flights from Linden Airport (KLDJ) in a Piper Cherokee PA-28. The Hudson River corridor, the Statue of Liberty, the Manhattan skyline. About 45 minutes of air time. Day or night slots available; the Romantic Date Night package includes a longer route and timing optimized for the visual moment. Book a Night Tour or call (347) 727-0050.
2. A baseball game (Yankees or Mets)
Yankee Stadium for the venue, history, and pre-game in the Bronx. Citi Field for the food and shorter lines. Bleacher seats are $30-50.
3. A Knicks or Nets game
Madison Square Garden for the Knicks (history, location, $80+). Barclays Center for the Nets (newer, $50+, lower-key).
4. A rangers or Islanders hockey game
Same venues, lower secondary-market prices than basketball.
The active ones
5. Royal Palms Shuffleboard Club (Gowanus)
A 17,000-square-foot shuffleboard hall with ten courts, three bars, rotating food trucks. Reservations on weekends.
6. An escape room
Mission Escape Games (Midtown), The Escape Game (multiple locations). 60-90 minutes, $30-50/person. The collaborative element is the appeal.
7. Bowling at Brooklyn Bowl
Bowling, bar food, live music venue. The combination is the point. Reservations.
8. Bouldering at the Cliffs (LIC) or Brooklyn Boulders
Indoor climbing for beginners. Day passes around $30. Wear something you can move in.
The food-based dates
9. A taco crawl through Sunset Park or Bushwick
Tacos El Bronco, Tacos Matamoros, Don Paco Lopez. $4-6 per taco. Eat three places in an afternoon.
10. A dumpling crawl through Flushing
Joe's Shanghai for soup dumplings, Lao Dong Bei for Northeastern Chinese, Nan Xiang Xiao Long Bao for the focused version. $5-15 per place.
11. A pizza tour (specifically: Brooklyn)
Lucali (Carroll Gardens), Di Fara (Midwood), L&B Spumoni Gardens (Bensonhurst). Eat one place per day; don't try all three in one outing.
12. A late-night dim sum run at Wo Hop
Open until 3 AM. Mott Street basement. Cash only. Specifically NYC.
The unobvious ones
13. The Comedy Cellar
Two-drink minimum, reservations required, lineup unannounced. Sit at the front for the best experience.
14. A walk in Greenwich Village late at night
Specifically: between 11 PM and 1 AM. The streets are quieter than the daytime crowds. The bars, the brownstones, the bookstores still lit. Free.
15. A weekend somewhere in NYC neither of you have been
The Bronx (Arthur Avenue for Italian, the Botanical Garden, the Yankees). Staten Island (the ferry, Snug Harbor, the lighthouse museum). Most NYC residents don't know their own outer boroughs. Treat one like a foreign trip.
What to pick
For the first few dates: a casual food crawl or a rooftop. For special occasions: the flight (#1) or a tasting menu. For the date that becomes a story: something he didn't see coming and that's specific to NYC.