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.
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.
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!"
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.
While shooting the movie Marley & Me with Owen Wilson in Miami, Aniston, 39, is linked to John Mayer, 30. Paparazzi even snap photos of them embracing on a Miami beach. In August, their romance fizzles, but they briefly reunite before calling it quits after attending the Academy Awards together in 2009.
Sporting only a patriotic tie, Aniston bares all on the cover of GQ. On the subject of Angelina Jolie–who the actress called 'uncool' in the December issue of Vogue–she jokes, "The funny thing is, people don't realize we all go away to The Hamptons on the weekends." With the No. 1 flick Marley & Me, Aniston bests Pitt's drama The Curious Case of Benjamin Button that opened on the same day.
After starring with Gerard Butler in The Bounty Hunter, Aniston keeps the laughs coming – this time with Jason Bateman in The Switch. The film, about a woman who has a baby via artificial insemination, draws criticism from Fox News anchor Bill O'Reilly, igniting Aniston to reply: "For those who've not yet found their Bill O'Reilly, I'm just glad science has provided a few other options."
Aniston enjoys a dinner date with Wanderlust costar, newly single Justin Theroux, in Los Angeles before attending an afterparty for the MTV Movie Awards together weeks later. But their romance isn't cemented until photographer Terry Richardson snaps the couple snuggling in New York City. It's clear Aniston is "very happy with Justin," says a source close to the actress. "He's a great guy."
BIOGRAPHY (top to bottom): Malibu Media; Mario Testino/Vanity Fair; RAMEY; George Burns/Harpo Productions/AP; PRNewsFoto / glaceau; Fame; Courtesy Terry Richardson