Shortly after her divorce from Brad was finalised, Jennifer moved to Chicago to shoot the aptly-titled movie The Break-Up. But despite the subject matter, Jen ended up hooking-up with funnyman co-star Vince Vaughn. They dated for 12 months before calling it quits.
People date, and sometimes it works out, and sometimes it doesn't, said Vince after their split. I still talk to her constantly. I have a real, genuine connection with Jen.