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Date Night in Boston

Five date nights we’d actually suggest to a friend, from free trivia to a big show at The Wilbur. Ticket prices are for two, straight from each venue’s site (checked October 13), and don’t include food or drinks. All of them are indoors.

Free art, then stand-up in the Seaport

Start at the ICA, which is free for everyone Thursdays from 5 to 9 PM (reserve the free tickets). Then walk about 15 minutes to Laugh Boston for the 7 PM show.

  • Tickets for two: about $66–70 plus fees for the comedy; the ICA is free.
  • Book: ICA free tickets and Laugh Boston seats (general admission, so arrive early).
  • Know: Laugh Boston is 16+ and checks IDs; no food or drink minimum.

Dinner and improv in the North End

Improv Asylum on Hanover Street runs its main stage show most Wednesday through Saturday nights, and sells dinner-and-show packages that pair a 5 PM three-course dinner nearby with the show. Through October the main stage show is the Halloween revue.

  • Book: the package or show tickets through Improv Asylum.
  • Know: shows run about 90 minutes with a short intermission; arrive 30 minutes early. Most are listed 16+.

A folk show in Harvard Square

Club Passim is a basement folk club in Cambridge where you sit close to the stage. There’s a kitchen with a dinner menu, so the whole date can happen in one place.

  • Tickets for two: usually $60–80, fees included (members pay less).
  • Book: online or at the box office, which opens an hour before the show and skips the $3 processing fee.
  • Know: all ages; no paper tickets, just give your name at the door.

Trivia or karaoke, no cover

For a no-cover date, Club Café in the South End runs free trivia Tuesdays from 8 to 10 PM, and on Wednesdays you can pick karaoke (8 PM to midnight) or the Broadway Hump Day sing-along (7:30 to 10:30 PM). More options are on the trivia and karaoke pages.

  • Tickets for two: free; you pay only for food and drinks.
  • Book: Club Café takes table reservations online.

A big-name show at The Wilbur

The Wilbur on Tremont Street books touring comedians, bands, live podcasts and storytelling nights like The Moth.

  • Book: Ticketmaster or the box office (Tuesday–Saturday, noon to 6 PM).
  • Know: bags are searched and there’s no coat check; no outside food or drinks, including water bottles. Parking is validated at the 660 Washington Street garage.

None of these quite right? See what’s on this weekend, or the free stuff.