Remind yourself Chinatown doesn't totally suck
T stop: South Station (Red Line)
There really is nothing not to love about Chinatown (unless you’re a vegan), but the place wins special accolades for having long saved the city from its early-to-bed self. Wander the streets at 2:01am and you’ll shake your head at how much remains open. Chau Chow City and Peach Farm are two faves (ask for “cold tea” and see what happens). And don’t forget South Street Diner, one of the city’s rare, greasy favorites that's open 24 hours.
Make your move on the roof of Tisch Library
T stop: Davis Square (Red Line)
Sure, there’s probably no cheesier Tufts University dating maneuver than taking a potential paramour up to the library roof at night to see the city skyline. BUT: the rooftop is also open to anyone willing to climb the outdoor stairs. And it’s actually kind of cool. Also... free!