From Brad Pitt to Justin Theroux: A Look Back at Jennifer Aniston's Former Flames

Following Jen and Justin's split, we're taking a look back at the loves of the actress's life

01 of 08

BRAD PITT

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Tony Barson/WireImage

Their lavish July 2000 Malibu nuptials cemented Brad Pitt and Jennifer Aniston as Hollywood's golden couple. But five years later, Aniston files for divorce amid rumors that Pitt had developed off-screen chemistry with his Mr. & Mrs. Smith costar Angelina Jolie, whom he went on to wed in 2014. Pitt and Jolie call it quits in September 2016.

02 of 08

VINCE VAUGHN

VINCE VAUGHN
Eliot Press/Bauer-Griffin

Life imitating art? By June 2005, Aniston rebounds with Vaughn, her costar in The Break-Up. The two share affectionate dates in his Chicago hometown and jet-set to her favorite Mexican getaway, fueling reports of an impending wedding. By the end of 2006, the couple break up.

03 of 08

PAUL SCULFOR

PAUL SCULFOR
Luis Martinez/Splash News Online; Fame

Aniston shares a romantic dinner in May 2007 with a mystery man, later identified as British model Sculfor, who has also been linked to Cameron Diaz. But by August, his rep tells PEOPLE he and Aniston are just "friends."

04 of 08

JOHN MAYER

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Kevin Mazur/VF/WireImage for Vanity Fair

In 2009, the rocker helps Aniston celebrate her big 4-0 with a very special present: a song. Following a year of off-and-on dating, the couple call it quits for good a month after attending the 2009 Academy Awards together – though Mayer later admits he's "never really gotten over it."

05 of 08

GERARD BUTLER

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Carlos Alvarez/Getty

The Bounty Hunter costars' flirtation seems to play out when the cameras aren't rolling: They are spotted hand-in-hand (and with the Scottish actor's hand on her backside) as the two promote their film in 2009. "I literally became a member of her family," Butler told PEOPLE of their relationship a year later.

06 of 08

BRADLEY COOPER

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First linked in 2009 when they costarred in He's Just Not That Into You, talk of an Aniston-Cooper romance reignites after the actor's 2011 split from longtime girlfriend Renée Zellweger. "Jen always had a soft spot for Bradley, and she thinks he is very attractive and charming," a source tells PEOPLE, but soon after, Aniston steps out with Justin Theroux.

07 of 08

NORMAN

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X17online

It was total puppy love for Aniston and her beloved Welsh corgi-terrier mix, who died in 2011 at age 15. "He's my baby boy. Norman goes with me on location – I've got to take Norman," she told PEOPLE of the most enduring, steady relationship in her life. She later debuts an inked commemoration for her furry friend.

08 of 08

JUSTIN THEROUX

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Broadimage/REX/Shutterstock

What started as summer lovin' in May 2011 turned into a happy ending for America's sweetheart when Theroux popped the question to Jennifer Aniston the following August. Their whirlwind romance has taken them from the red carpet to the beaches of Cabo San Lucas, Mexico before tying the knot in 2015.

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