The Rapper: Diddy
The Singer: Jennifer Lopez
Why They Should've Hooked Up: Once J. Lo and Marc Anthony broke up, you just knew the "J. Lo is getting back together with Puffy!" stories were going to fly. And they did. And then, for whatever reason, they stopped. C'mon, Jenny. You were the only girl who could keep Diddy tamed. And, Diddy, J. Lo still looks as bad as she ever did (or, at least, better than Cameron Diaz!). Why not reunite for old times' sake?