Squirrel killing?? SQUIRRELS? WTF?! This chick has got to GO!OK, back to my nuts, and I don't mean the IMDB board.
I live in Chicago as well but grew up in Detroit, and if he met her there, who knows, may be a boredom thing. It isn't the most happening place to find things to do (sorry Motown, I still love you).
I feel you on the lack thereof stuff to do. After being in a long term he's having fun. Best way to get over someone is by being with somebody else for about 3 to 6 months til the ghosts start to creep in.
By the way, I love Motown too and Detroit just for that, forever ever!