Vince Vaughn After her split from Pitt, Aniston began dating her "The Break-Up" costar, Vince Vaughn. The two were together for a year before going their separate ways in December 2006. Of dating Aniston, Vaughn told Playboy (via E! News), "You know, she's great. For me personally — and I think most well-known actors who are together feel this way — I never enjoyed the paparazzi side of it." Image Source: Getty / Clive Brunskill