What to Do With 1 Night in Boston Next Thursday?

Asking for a friend.
  1. Friend is:
  2. Married
    4 kids
  3. White
    Male
  4. Mature
    Between 39 and 40 years old
  5. Staying downtown for work
    Hasn't ventured into Boston in 12 years
  6. Into comedy, sports, movies
    And listing
  7. OK with eating alone in public
    Movies too
  8. Any and all suggestions welcomed and appreciated!
    I'll make sure he gets them.
  9. Go to the airport and buy a cute sweatshirt with Boston written on the front?
    My one and only, tried and true Boston experience, but it was pretty satisfying. (Actual sweatshirt not pictured)
    Suggested by   @jennifergster
  10. Download the @Trill app for obscure and awesome events in Boston
    Suggested by   @mallofamanda
  11. No Name Restaurant
    Checkered table cloths, 70 year old Greek guys sitting at a corner table (and looking like they've been there for decades), all the waitresses are over 50 and the sea food is bangin'. You can wear a bib and no one will judge you. Also has validated parking. I think this might be a really gauche suggestion (at least the Yelp reviews seem to say so) but I'm low-brow and unashamed. I loved it.
    Suggested by   @amieshmamie
  12. Eat Belgian-style fries and waffles at Saus then go to SketchHaüs at ImprovBoston
    Suggested by   @Trill
  13. Or the Main Stage show at Improv Asylum
    Suggested by   @Trill
  14. I agree with @Trill Saus also has beer ice cream floats which are the bomb! And improv asylum is like 1000 feet away from modern pastry which has amazing desserts!!! 😊
    Suggested by   @d33rmngr
  15. Cafe Polonia
    Badass little Polish spot I go to every time I'm in town. Family owned and run place.
    Suggested by   @culture_czar
  16. Since you said movies...there's an awesome one screen indie theater in Cambridge called The Brattle Theater. They always have something interesting showing whether new & boundary pushing or classic films. It's maybe a two block walk from the Harvard Square station on the Red Line.
    Suggested by   @culture_czar