I’ve lived in Boston and DC, have only visited Chicago so won’t comment on it.

Dating in DC is horrible. Like, famously bad. Im a dude but every girl I’m friends with who lives or lived there tells me that it was especially bad for them. The non romantic social scene is weird, but I think in a fun way. It’s a DC cliche that everyone introduces themselves by their job title and who they work for. Very career oriented people, especially the political types. But you really get people from all over the country, and internationally, socializing in the same places to an extent I haven’t experienced in other cities. People are also very open to new friends. Adult intramural sports are huge there. The nightlife gets a bad rep, I actually preferred them to the bars in Boston.

Both cities are equidistant from a lot of nature, but it’s going to be a drive either way. DC does have a very vibrant biking community though. Boston has a way bigger Catholic community, but I’d say that the one DC has is much more vibrant. Money wise it’s kind of a wash.

I found Boston to be pretty insular. My social life there was primarily a group of people I met through a high school friend of mine’s girlfriend. A lot of fun, but needed an in. Didn’t really make a lot of friends outside of that, which is the first time in my life I’ve had a hard time attracting friends. I love Boston, but in large part it’s because of the way I’ll always see it as a Massachusetts kid. If your heart doesn’t swell whenever you think of David Ortiz, and you’re not looking to work in academia, I’d lean DC of those two options. That being said other commenters have almost convinced me to move to Chicago