Jennifer Aniston’s Journey For Love: The Star’s Exes in Pictures

Jennifer Aniston

Jennifer Aniston | Jason Merritt/Getty Images

Jennifer Aniston rose to fame as the witty, proud, slightly-spoiled Rachel on Friends. Since then she’s made us laugh, cry, and laugh so hard we cry with films like Along Came PollyMarley and MeCake, and We’re the Millers.

The incredibly popular actress captured viewers’ hearts with her talent, philanthropy, and inspiring a healthy lifestyle.

Meanwhile, she captured the hearts (and affections) of a few very famous men. Fans remained invested in Aniston’s love life, particularly following her messy, publicized split from movie star Brad Pitt.

Tate Donovan

1997 Jennifer Aniston and Tate Donovan in "Friends" ("Rachel's Crush").

Jennifer Aniston and Tate Donovan in “Friends” (“Rachel’s Crush”). | “Friends”

One of Aniston’s first serious relationships was with an on-screen fling as well. Tate Donovan played Joshua, a wealthy divorcee who Rachel crushes on and eventually dates.

Aniston and Donovan started dating in 1995 and were together when he was cast as her Friends love interest. They got engaged in 1997 for a short amount of time before calling off the wedding and their relationship in 1998.

Brad Pitt

Brad Pitt with Jennifer Aniston

Pitt and Aniston’s romance became a pop culture phenomenon | Ucy Nicholson/AFP/Getty Images

Despite a short rumored fling with frequent co-star Paul Rudd, Aniston’s next (and arguably most) serious relationship was with Brad Pitt in 1998. The couple’s individual star power increased drastically once they were linked to one another. Their agents set them up on a date in 1998 and they were engaged a year later.

The two married in a high-profile, lavish Malibu wedding in 2000 complete with media-blocking tents and fireworks to cap the night. The couple became a Hollywood icon, inspiring labels like the “It” couple and a “rare Hollywood success.” Pitt, like a few of Aniston’s other partners, made an appearance on Friends. He guest-starred in the episode “The One with the Rumor.” Pitt-Aniston fans went crazy watching his character bash Rachel Green while she vied for his approval.

Rumors of trouble in paradise brewed in January 2005 and the two quickly announced their separation. They divorced that October amidst media speculation that Pitt cheated on Aniston with his Mr. & Mrs. Smith co-star Angelina Jolie. These rumors were ultimately confirmed when Pitt and Jolie publicly dated quickly after the split, inspiring fans to “pick sides” with paraphernalia like “Team Jolie” and “Team Aniston” T-shirts.

Vince Vaughn

2006 French Open - Day Fifteen

Jennifer Aniston and Vince Vaughn attend the men’s singles final on June 11, 2006 in Paris, France. | Clive Brunskill/Getty Images

Aniston quickly began dating Vince Vaughn following her official divorce from Pitt. The two met on the set of their movie, The Break Up, and ultimately they did just that, a year later. The two kept their relationship as private as possible, and the insane media attention Aniston garnered was one thing Vaughn didn’t like about dating her.

“You know, she’s great,” he told Playboy mag. “For me personally — and I think most well-known actors who are together feel this way — I never enjoyed the paparazzi side of it. You like someone and you’re spending time with them; that’s separate and that was all fine. But I really spent most of that time finding ways not to be drawn into the attention.”

While fans argued the relationship screamed “rebound,” Aniston shared what Vaughn really was to her — “a defibrillator.”

“He literally brought me back to life. My first gasp of air was a big laugh! It was great. I love him. He’s a bull in a china shop. He was lovely and fun and perfect for the time we had together. And I needed that. And it sort of ran its course,” she told Vogue following their 2006 split.

John Mayer

jen aniston john mayer oscar party

Jennifer Aniston and John Mayer at the 2009 Vanity Fair Oscar Party | Alberto E. Rodriguez/Getty Images

Aniston dated John Mayer on and off for 11 months in 2008 (this was pre-“Dear John,” but after the singer was recognized as a womanizer to be watched). Mayer confirmed that while the relationship didn’t pan out, the two were very much in love, telling Playboy, “I wouldn’t undo it … Because if it had worked out, I would have reaped the benefits. I would be sitting here saying, ‘What I have when I go home is the thing I’ve always wanted.'”

It turned out their breakup was a result of conflicting plans rather than Mayer’s infamous “player” behavior. He alluded to having strong feelings for Aniston in an interview after they split. “Have you ever loved somebody, loved her completely, but had to end the relationship for life reasons?” he explained in the interview.

Justin Theroux

Jennifer Aniston and Justin Theroux pose on the red carpet.

Jennifer Aniston and ex-husband Justin Theroux | Mark David/Getty Images

Aniston met actor Justin Theroux first on the set of Tropic Thunder in 2007 and again on 2011’s Wanderlust. Theroux was dating his girlfriend of 14 years, Heidi Bivens, but the two broke up shortly after. Aniston and Theroux became a rumored item as of May 2011 and made official appearances as a couple that June. They moved in together, adopted a pit bull, and continued to support one another’s careers.

“Having experienced everything you don’t want in a partner over time, it starts to narrow down to what you actually do want,” Aniston told InStyle in February 2012. “As I get older I realize what qualities are important in love and what suits me. And what I won’t settle for.” Aniston accepted Theroux’s marriage proposal six months later.

 The couple had a long engagement and married three years later in a secret backyard ceremony complete with an “ironclad prenup” and close friends like Courteney Cox, Lisa Kudrow, Ellen Degeneres, and officiate Jimmy Kimmel.

Aniston and Theroux’s enviable love story comes to an end in 2018 on reportedly good terms.

“This decision was mutual and lovingly made at the end of last year,” the statement read. “We are two best friends who have decided to part ways as a couple, but look forward to continuing our cherished friendship.”

Aniston isn’t linked to any potential partners at the moment, but the important news is her continued commitment to her philanthropic efforts with nonprofits like St. Jude’s Research Hospital, the American Red Cross, and Doctors Without Borders.

“We are complete with or without a mate, with or without a child. We get to decide for ourselves what is beautiful when it comes to our bodies … We don’t need to be married or mothers to be complete. We get to determine our own “happily ever after” for ourselves,” Aniston wrote in her 2016 essay for Huffington Post “For the Record.”

Honorable mentions:

  • Paul Sculfor: Aniston reportedly dated the model for a few months in 2007
  • Orlando Bloom: The media speculated Aniston and actor Bloom dated in 2007. It was never confirmed and never denied — but wow, we hope it happened
  • Gerard Butler: Aniston reportedly dated her The Bounty Hunter costar for a few months in 2009

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