Five Times Jennifer Aniston Co-Starred With Her Real-Life Loves

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Jennifer Aniston has made headlines for her love life as much as her movie and TV career. The former Friends star, who turns 50 on February 11, has dated Counting Crow frontman Adam Duritz and singer John Mayer, but she’s also made beautiful music with several famous men who were her co-stars on both the big and small screen.

One of Jennifer Aniston’s most memorable romantic relationships was with actor Tate Donovan, whom she dated for three years in the 1990s. During her reign as Rachel Green on Friends, Aniston actually broke up with Donovan just weeks before he guest-starred on the show as Joshua Burgin — Rachel’s personal shopping client and major crush — for six episodes on the NBC sitcom.

In the hilarious Friends arc, Rachel did everything she could to attract Joshua, including donning a high school cheerleading outfit to catch his eye. But Donovan told Us Weekly he was “dying inside” during his six-episode stint on Friends because he and Jennifer Aniston were in the middle of a brutal, real-life breakup. The actor also hinted that the arc was cut short because it was just too “painful and tough” for the exes.

“That was tricky to sort of act, and act like we are just meeting each other, and falling in love, or whatever, interested in each other, when we’re sort of breaking up. That was just tough,” Donovan admitted.

In 1998, Jennifer co-starred with Paul Rudd in the film The Object of My Affection. But Glamour reports the two stars briefly became a real-life thing. Although the short romance didn’t work out, the two stars remained friends.

Paul Rudd was later cast on Friends as Phoebe’s (Lisa Kudrow) boyfriend Mike Hannigan. In addition, he reunited with Aniston on the film Wanderlust, where the actress met and fell in love with future husband Justin Theroux. While promoting the film, Jen was asked if it felt weird to kiss Paul Rudd on camera.

“Nah. I’ve kissed him for years,” she told GQ, while Rudd added, “We’ve made out for decades.”

Early on in her marriage to Brad Pitt, Jennifer Aniston traded lines with her real-life husband in the 2001 Friends episode The One With the Rumor. Pitt made a surprise guest appearance as Will Colbert, Rachel Green’s former high school classmate, in the Thanksgiving-themed episode.

Pitt later addressed the surprising cameo in an interview with Entertainment Weekly, revealing that when he first started out as an actor, agents were trying to get him into sitcoms due to his good looks, but he wanted to make movies. He made a rare exception to work with his then-wife on Friends, telling EW of the ensemble cast, “I like those guys. They’re a great bunch of guys.” Brad Pitt and Jennifer Aniston divorced in 2005, but they will forever share a page in Friends history.

In 2006, Jennifer Aniston literally threw herself into her work after her breakup from Pitt. The actress teamed up with Vince Vaughn for the big screen comedy-drama The Break-Up, and they struck up a real-life romance.

Aniston later told Vogue that her relationship with Vince Vaughn brought her “back to life” after her heartbreak with Brad Pitt.

“I call Vince my defibrillator,” Jennifer Aniston told Vogue. “He literally brought me back to life. My first gasp of air was a big laugh! It was great. I love him… He was lovely and fun and perfect for the time we had together. And I needed that. And it sort of ran its course.”

In 2009, love happened for Jennifer Aniston once again. When shooting the film Love Happens in Canada, rumors swirled that Aniston and her co-star Aaron Eckhart were an item.

According to Marie Claire UK, the two were “inseparable” while making the film, with an on-set insider dishing, “Jen’s entire reason for doing this movie was Aaron. …They genuinely enjoy each other’s company.”