I'm actually embarrassed over how much attention I've been playing to the Bridgeport locals, the ones whom I would never play myself. For most EA sims in most other worlds, I usually just don't care so much. In my game, Kai lives in the sparse looking cabin under the bridge. He became Lola's toy boy, though. I arranged a regularly occurring money transfer between them because he has poor job performance and would go bankrupt on his own otherwise. Their relationship never tanked, and they are still Romantic Interests even though I cut off the flow of money some time ago as he transitioned into his full time film career and began making enough to support himself properly.
Matthew and his pregnant girlfriend still like each other but just broke up for no reason I can figure (throws rule book out the window, hope it didn't hit anyone). I give up. :D