5 Other Celebs Jennifer Aniston Could Have Ended Up With

Vince Vaughn Vaughn was Aniston’s first serious post-Pitt relationship. The two met on the set of The Break Up during the summer of 2005 but initially denied anything was going on. After pictures emerged of the two kissing in Vince’s beloved Chicago, they were a bit more open about what was going on, especially after engagement rumors began making the rounds. They each feverishly denied there were plans to move forward anytime soon, and those claims were validated when they officially broke up after a little more than a year of dating.