Jennifer Aniston's Relationships

Getty Images
Even more than her hair, her role on Friends and the string of mediocre romantic comedies that followed, Jennifer Aniston is more notorious for her series of failed romances (sorry, Jen). Whether it’s high-profile musicians or the biggest star in Hollywood, Jen’s had (and lost) her fair share of them all.
 
Just a budding starlet in the early 90s, Aniston’s love life wasn’t getting as much attention as her “Rachel” haircut. She dated Adam Duritz, the lead singer of Counting Crows for a year during her first season on the hit sitcom, but she soon moved on to Tate Donovan.
 
Her three-year relationship with Donovan was serious enough to land her an engagement ring, and him a guest spot on Friends—the ultimate sign of lasting love. But they split in 1998, and she embarked on her most high-profile romance to date with Brad Pitt.
 
The two met through their agents and enjoyed a two-year romance before he popped the question. Their 2000 wedding was just as much of a fairytale as their careers, replete with lobster, champagne and fireworks. But their split five years later wasn’t quite as storybook. He suddenly filed for divorce from a clearly shell-shocked Jen and went on to start a very public romance with his sexy Mr. and Mrs. Smith co-star, Angelina Jolie.
 
Aniston promptly rebounded with her The Break-Up co-star Vince Vaughn, and the two were hot and heavy for a year, even battling rumors of an engagement, before calling it quits in 2006. Vaughn ended up marrying real estate agent Kyla Weber in 2010. By the time their relationship was over, Jen was getting a bit of a reputation for being unlucky in love. 
 
After a brief stint with British model Paul Sculfor, who kept his dating stock up by getting with Cameron Diaz afterwards, Jennifer set out on another high-profile courtship with musician John Mayer. The pair broke up and reconciled before finally ending it in March 2009. Some said it was because of Mayer’s incessant tweeting, while others blamed Aniston’s high-maintenance lifestyle. But years later, in very revealing interviews with Playboy and Rolling Stone, Mayer admitted that he still loves Jen, saying, “I’ve never really gotten over it. It was one of the worst times of my life.”
 
Since then she reportedly went on several failed dates with Bradley Cooper, who opted to start a relationship with Renee Zellweger instead, before reputedly romancing her bad boy, Scottish Bounty Hunter co-star Gerard Butler. Their romance was never confirmed, and she continues to be plagued by rumors of unconfirmed relationships every time she’s seen in public with any member of the opposite sex.


     
Email This

MORE ABOUT Jennifer Aniston

The latest stories, biography, photos, videos, and more. Read more about Jennifer Aniston Li Latest News Jennifer Aniston Makes A Permanent Mark On Hollywood (Photos)


Sites We Love