#3: Jennifer Aniston and Brad Pitt

Duration of Relationship: 7 years (1998–2005)

The breakup between Jennifer Aniston and Brad Pitt in 2005 shocked fans worldwide. Once considered Hollywood’s golden couple, their marriage of five years ended amid rumors of Pitt’s growing closeness with Angelina Jolie on the set of Mr. & Mrs. Smith.

While Aniston publicly handled the split with grace, she later admitted it was excruciating, wildly as rumors of an affair swirled. Despite the media frenzy, both stars remained relatively quiet on the details. Their breakup marked a turning point in both their lives, with Aniston focusing on her career and personal growth while Pitt moved forward with Jolie.