Vince Vaughn: The Beginning
Her age: 36
Duration of Relationship: 2005-2006
Vince Vaughn and Jennifer Aniston began their relationship in 2005 on the set of their film The Break-Up. Both were navigating personal transitions then; Aniston was freshly divorced from Brad Pitt, and Vaughn was one of Hollywood’s most eligible bachelors.
Their chemistry was immediate, both on and off the screen, sparking rumors of a real-life romance. They were often seen enjoying each other’s company during and after filming. Aniston later described Vaughn as her “defibrillator,” noting how his humor and charisma helped revive her spirit during a difficult period.