New York is a city that rewards people who plan something better than "a bar in the East Village." Here are eleven date ideas that actually give you something to talk about.
1. The High Line, north to south, ending at Chelsea Market. A walk with a built-in destination, which takes all the pressure off deciding when it ends.
2. The Staten Island Ferry at dusk. Free, twenty-five minutes each way, and a skyline view people pay a great deal of money for elsewhere.
3. A small museum instead of a famous one. The Morgan Library, the Frick, the Neue Galerie - quiet enough to talk in, small enough to finish, and far more memorable than an exhausted lap of the Met.
4. Governors Island for the afternoon. A short ferry, bikes, and enough space that a slow conversation has somewhere to go.
5. A basement jazz room. Smalls or the Village Vanguard - close quarters, no phones, and a shared thing to react to that isn't each other.
6. Prospect Park rather than Central Park. Less crowded, more forgiving, and the walk out to it is half the date.
7. A food market with a lot of choices. Smorgasburg in season, Essex Market when it isn't - grazing is a much easier first date than a fixed table for two hours.
8. The Brooklyn Bridge into Dumbo, at the right time of day. Early morning or late evening, when it's walkable rather than a slow-moving crowd.
9. A comedy show on a weeknight. Low stakes, genuinely funny, and you learn a lot about someone from what makes them laugh.
10. The Strand, then wherever you end up. Forty-five minutes in a bookshop tells you more about a person than an hour of polite questions.
11. A supper club or communal table. Forces conversation with each other and, often, with whoever is sitting either side - a good test of how someone handles a bit of unpredictability.
The thing that actually matters
The best date ideas aren't the most impressive ones - they're the ones that give two people something to do together, react to together, and talk about afterwards. New York makes that unusually easy, if you resist the urge to book the loudest room in the city.
Elsewhere: London, Los Angeles, Dubai. Related reading: Getting Back Into Dating: 5 Tips to Start.
