Do You Know Jennifer Aniston’s Most Famous Exes?

She’s been Hollywood’s golden girl for decades, with ageless beauty, humor, and charm to spare. Jennifer Aniston has an impressive resume in film and television as well as dating – she’s dated some of the biggest names in the business. With her recent split from actor Justin Theroux still fresh in the public’s mind, let’s review a few of Aniston’s most famous exes.

Jennifer Aniston dated a famous funnyman

Jennifer Aniston is well known for her sense of humor, and long before she met Justin Theroux, she was paired up with one of the biggest names in comedy. Aniston met Vince Vaughn, best known for movies like Wedding Crashers, in 2005 and the two dated briefly before ending things in 2006. They even starred in a movie together, The Break-Up, about an established couple who go through a painful split.

She was open about how much she relied on Vaughn to make her laugh, especially considering she had recently ended things with ex-husband Brad Pitt. Their 2006 split was harmonious, and Vaughn admitted in a later interview that while he and Aniston got along very well and that she’s a wonderful person, the public attention surrounding their relationship got to be too much to handle.

Jennifer Aniston and her musician boyfriend

While famous musician John Mayer is known to be a popular ladies man with exes that include Taylor Swift and Katy Perry, one of his most high-profile relationships was with Jennifer Aniston. The two dated on and off from early 2008 to early 2009, and in spite of the 10-year age gap between the pair, they were hot and heavy for each other. After their split, Mayer reminisced that he was probably the reason they didn’t work out, claiming that he was a narcissistic jerk.

Jennifer Aniston’s most famous relationship

Undoubtedly, Jennifer Aniston’s most famous relationship was her marriage to Brad Pitt. The two started dating in the late ’90s and got married in 2000. For years, they were Hollywood’s “it” couple, and their golden good looks made them the star of any event or red carpet they visited. The good times didn’t last, however, and the couple split in 2005 after it was revealed that Brad Pitt had been conducting an affair with his Mr. & Mrs. Smithcostar, Angelina Jolie.

The public still holds onto the idea of Aniston and Pitt as a couple, and after Pitt split from Jolie in 2016, the rumor mill started working overtime, speculating that the former flames could one day reunite.

Justin Theroux and Jennifer Aniston

Aniston’s most recent famous break up is with actor Justin Theroux. The two met in 2010 and were together for years before getting married in 2015. They seemed happy as could be, but the pressures of a long-term relationship in Hollywood took a toll, and in late 2017, Aniston and Theroux announced their divorc. Reportedly, their drastic differences in lifestyle caused the break up, and although neither Aniston or Theroux have commented since the split, fans are still wondering where it all went wrong.

Jennifer Aniston is still beautiful, and at 50 years old, is in the prime of her life. After her big birthday party, when a number of her famous exes showed up to party and celebrate the birthday girl, fans have been wondering who her next relationship will be with. Although popular opinion most consistently seems to pair her with Brad Pitt, it’s most likely that Jennifer Aniston, who has never played by the book, will end up surprising her fans with a boyfriend that might seem totally out of left field.