Date Night Ideas in New York

Setup.A wet morning or afternoon, one umbrella, nothing booked. Both buildings are free to walk into. Check the library's hours and tour times before you go.

1. Meet between the lions on the library steps on Fifth Avenue. Patience is on the south side, Fortitude on the north.
2. Head inside to the Rose Main Reading Room, which runs nearly the length of a football field. People are working, so look up, stay quiet, and save the commentary for the stairs.
3. Browse whatever free exhibition is on, or join one of the daily building tours if the timing works.
4. Walk east on 42nd Street to Grand Central. In the Main Concourse, look up: the painted sky is reversed left to right, all except Orion, and nobody has ever corrected it. Then find the small dark patch near the crab of Cancer that restorers left uncleaned on purpose.
5. Head down the ramps toward the Dining Concourse. On the landing under the tiled arches, stand in diagonally opposite corners, face the wall, and whisper something you have been meaning to say.

Talk about:That ceiling has been backwards for more than a hundred years and people love it anyway. What is one of our quirks you would never want fixed?

Setup.A warm, clear day, a packed lunch, water, and a blanket. Ferries leave every day from the Battery Maritime Building, right next to the Staten Island Ferry terminal, and on weekends from Pier 6 in Brooklyn. The island is open year round; check the ferry schedule and fares before you go.

1. Take the ferry from the Battery Maritime Building. The crossing to Soissons Landing is about seven minutes, so stand at the rail and watch Manhattan shrink.
2. Walk south to Hammock Grove, ten acres of trees with around fifty hammocks, and claim one. If they are all taken, carry on to Picnic Point at the southern tip, where there are picnic tables by the water.
3. Climb Outlook Hill, the tallest of The Hills, for the view over the harbor to Lower Manhattan and Brooklyn.
4. Loop back along the waterfront promenade that rings the whole island, then pass the two old forts, Fort Jay and Castle Williams, at the north end on your way to the ferry.

Talk about:If we lived on an island with no cars for a year, what would you miss first, and what would you not miss at all?

Setup.The A train to 190th Street, comfortable shoes, and an unhurried morning. The park is free. The museum is ticketed, and the Met's long standing policy lets New York State residents pay what they wish, so check the current terms and hours for the Cloisters on the Met's site before you go.

1. Take the A train to 190th Street, ride the elevator up to Fort Washington Avenue, and walk north to the tall stone pillars at Margaret Corbin Circle, the park's southern entrance.
2. Step into the Heather Garden just inside, the largest public garden in the city with unrestricted access, then follow the promenade north.
3. Stop at Linden Terrace, the stone lookout at the north end of the promenade, for the Hudson and the Palisades.
4. Carry on to the Cloisters. Find the Unicorn Tapestries first, then sit in one of the three cloister gardens, Cuxa, Bonnefont or Trie, and do not rush.
5. Walk back down through the park the same way, slower than you came up.

Talk about:Someone once bought the cliffs across the river so this view would stay wild. What is one thing in our life you would protect like that?

Setup.A clear morning, the R train to 25th Street, and a snack in a pocket. Admission is always free. Pick up a paper map at the entrance or use the free Bloomberg Connects guide, and check the entrance hours before you go.

1. From the 25th Street station, walk one block uphill to the main gate at Fifth Avenue and 25th Street. Look up at the spires for the parakeets.
2. Grab a map and pick a loose route toward Battle Hill rather than a strict plan.
3. At the top, find the Altar to Liberty and look out for the Statue of Liberty across the water.
4. Wander back by a different path, reading old headstones out loud and guessing at the lives behind them.

Talk about:By the early 1860s this place drew more than half a million visitors a year, second only to Niagara Falls in the state. What is an underrated place you would put on a list like that?

Setup.A summer afternoon into evening, the D, F, N or Q train to Coney Island Stillwell Avenue, and money for a ride or two each. The boardwalk is public and open year round, and walking into the Wonder Wheel's park is free, but the rides are seasonal and only run daily in summer; check hours before you go.

1. Ride to the end of the line at Coney Island Stillwell Avenue and walk toward the ocean to the boardwalk.
2. Ride the Wonder Wheel first. Sixteen of its cars slide along rails between the hub and the rim as the wheel turns, and eight stay fixed to the rim, so choose your nerve level together.
3. If you are both game, ride the Cyclone. If only one of you is, the other waits at the exit and films the face coming off it.
4. Walk east on the boardwalk toward Brighton Beach as the sky changes color, with the red tower of the old Parachute Jump behind you.
5. Take your shoes off for ten minutes on the sand before the long ride home.

Talk about:What is the scariest thing you have ever done just because someone you liked was doing it?

Setup.A clear evening, the 7 train to Vernon Boulevard Jackson Avenue (the first stop in Queens), and a jacket. The park is free and keeps daytime hours, so this is a sunset date, not a late night one; check hours before you go.

1. Get off at Vernon Boulevard Jackson Avenue and walk to the water.
2. Arrive well before sunset and pick a spot on one of the four piers.
3. Take turns finding the United Nations and the Empire State Building across the river while the light turns gold.
4. Stay until the skyline goes to silhouette, then head out as the park closes at dusk, past the Pepsi-Cola sign: 120 feet of red neon and a city landmark since 2016.

Talk about:Pick one lit window across the river and invent the whole life of whoever is behind it.

Setup.A drive-in cinema. A blanket for after sunset, snacks pre-packed.

1. Arrive 30 minutes early for a good spot.
2. Tune the radio to the listed FM frequency.
3. Recline seats for sightlines.
4. Coffee on the way home, drive-ins end late.

Setup.A wine region within driving distance. Designated driver or a tour shuttle. Light lunch booked at one cellar door.

1. Visit three vineyards. Buy one bottle from each.
2. Long lunch at the middle cellar door.
3. Walk between the buildings of the vineyard, slowly.
4. Drive home before sunset.

Setup.A baseball, basketball, hockey, or football game. Cheap seats, they are cheap for a reason and that's fine.

1. Get there 30 minutes before first pitch.
2. Hot dog and a drink each.
3. Stay through the seventh-inning stretch.
4. Walk to a bar near the stadium afterwards.

Setup.An omakase sushi counter. Booking required for most.

1. Sit at the counter, not a table.
2. Eat each piece in two bites max, within a minute.
3. Tip in cash if you can.

Setup.A pick-your-own orchard within an hour's drive. Autumn weekends.

1. Go early to skip the queue.
2. Pick more than you think, they keep.
3. Cider doughnut and hot apple cider before driving home.

Setup.A pair of indie record shops. A budget, one record each, no more.

1. Each picks one record for the other based on cover and sleeve only.
2. Reveal at the till of the second shop.
3. Buy them. Walk home.
4. Listen to both end-to-end that evening, in order.

Setup.A small brewery, cidery, or distillery with tastings. Many do a flight under $15.

1. Order the standard flight, not your usual style.
2. Score on smell, taste, finish.
3. Ask one staff member how they got into brewing.
4. Leave with one bottle from the flight.

Setup.A public ferry route or commuter boat. Most coastal and river cities have at least one.

1. Take the slowest ferry that leaves before sunset.
2. Sit on the upper deck if there is one.
3. Walk for 30 minutes at the destination, even if you do not stay.
4. Take the next ferry back. Watch the lights come on.

Setup.A country neither of you has been to. Music from there, food from there, a film from there.

1. Dress in something that fits the place, vague, fun, not a costume.
2. Cook (or order) one classic dish from the country.
3. Watch a travel show or short film set there.
4. Make a one-page "itinerary" you would do if you went next year.

Setup.Running shoes. A 5k loop. Water bottle.

1. Warm up with a 5-minute walk.
2. Run at conversation pace, if you cannot talk, slow down.
3. Sit on a bench halfway. Two minutes, no longer.
4. Coffee or smoothie afterwards.

Setup.A local observatory with public viewing nights. Layers, hot tea in a thermos.

1. Arrive at sunset to acclimatise.
2. Visit each scope at least once.
3. End at a 24-hour spot for hot food.

Setup.Most cities have a "free walking tour" with a tip-based model. Comfortable shoes, a refillable water bottle.

1. Get there 10 minutes early. Pick a guide whose intro you like.
2. Stay close enough to hear without crowding.
3. Tip the guide well at the end, these are real working people.
4. Eat at the most lived-in place near the end of the tour.