- 2005
Another Ending
After spending the New Year's weekend in the Caribbean with friends Courteney Cox Arquette and husband David Arquette, Aniston and Pitt announce that they are separating. They deny the split was a result of published reports linking Pitt to Jolie. Aniston files for divorce in March.
Rebounding with Vaughn
Reports emerge that Aniston and Vince Vaughn are dating while they film The Break-Up in Chicago. Although the costars deny a romance, Aniston and Vaughn return to the Windy City in October to shoot new scenes for the movie and are spotted kissing and being extremely affectionate.
For the Record
Aniston's highly anticipated interview in Vanity Fair hits newsstands. She tells the magazine that family planning had nothing to do with her split with Pitt ("That really pissed me off") and also takes a stab at Pitt's platinum hairdo ("Billy Idol called – he wants his look back"). By January, their divorce becomes official, Pitt adopts Jolie's children, and Jolie is pregnant with their first child together. Aniston tells Vogue, "Don't feel sorry for me!"
- 2006
No Wedding Bells
Aniston calls into The Oprah Winfrey Show after news outlets CNN and The Today Show falsely report that Aniston is marrying Vaughn. "It's just unbelievable," Aniston tells Oprah, who was tied into the wedding hub as reportedly throwing the $8 million bash. Back in September 2005, Aniston had dismissed the original rumors of romance with Vaughn on Oprah's show.
Box-Office Draw
Aniston and Vaughn's comedy The Break-Up makes $39.1 million its opening weekend. The real-life couple break up in December after more than a year together.
Broadway Debut
At the 6th Annual 24 Hour Plays on Broadway benefit, Aniston makes her Broadway debut portraying a single woman who attends an intimacy workshop with friends. Costar Rosie Perez tells PEOPLE: "We had a real boost from Jennifer Aniston. She was as sweet as pie."
- 2007
A Beautiful Pitchwoman
Aniston makes her fifth appearance on PEOPLE's Most Beautiful list, crediting yoga for keeping her toned and emotionally balanced. The fitness-buff, who is often photographed carrying smartwater, invests and appears in ads for the brand.
- 2008
Jen & John's Hot Romance
While shooting the movie Marley & Me with Owen Wilson in Miami, Aniston, 39, has an intimate lunch with John Mayer, 30. The two stars spend the entire weekend together, where paparazzi snap photos of them embracing on a Miami beach. Although the pair is inseparable for months, their romance fizzles in August.
Photo Credits
BIOGRAPHY (top to bottom): Malibu Media; Mario Testino/Vanity Fair; RAMEY; George Burns/Harpo Productions/AP; PRNewsFoto / glaceau; Fame
- Name
- Jennifer Aniston
- Birth Date
- February 11, 1969
- Birth Place
- Sherman Oaks, Calif.
- Heart Monitor
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John Mayer, ex-boyfriend (2008)
Paul Sculfor (dated briefly in 2007)
Vince Vaughn, ex-boyfriend (2005 to 2006)
Brad Pitt, ex-husband (1998 to 2005)
Tate Donovan, ex-boyfriend (1995 to 1998)
Adam Duritz, ex-boyfriend (1995)
Charlie Schlatter, ex-boyfriend (1990 to 1991)
