Jennifer Aniston has long held a reputation for being America’s sweetheart, and for good reason. The series that launched her career is a comfort show for many to this day, despite having concluded back in 2004, and the “Friends” alum has only garnered more fans as the years have gone by. She’s had her fair share of public relationships, and her high-profile marriage to Brad Pitt made her half of arguably one of the most popular A-list couples ever to hit the scene. Their seven-year relationship captivated (and in turn devastated) the world when it ended in 2005, but that was by no means the end of love for Aniston.
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The “Cake” star has been turning heads for decades after a stunning transformation that propelled her to celebrity stardom, so it’s unsurprising that she has had a healthy dating history both pre-and-post Pitt. From her controversial eight-and-a-half-year age gap with John Mayer to the shocking viral rumors of an affair with Barack Obama, she’s had no shortage of controversial relationships. However, you may not realize how many of Aniston’s romances originated on set. While it’s not uncommon for co-stars to spark in real life, workplace connections seem to be a trend for the star of “The Morning Show.” Read on to learn about which of her boyfriends (including one husband) she fell for while the cameras were rolling.
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She had a ‘torrid’ relationship with Charlie Schlatter while playing the role of his sister
Jennifer Aniston’s first taste of dating a co-star dates all the way back to 1990, when NBC’s sitcom spinoff of the hit John Hughes film “Ferris Bueller’s Day Off” cast her in the role of Jeannie, Ferris’ sister. She became entangled with the actor entrusted with playing the title role of Ferris Bueller, and rumor has it that their real-life relationship was pretty hot and heavy for a short time. That’s right — Aniston once dated her on-screen brother Charlie Schlatter.
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“GQ can exclusively report that everyone on set thought she was hot, including Schlatter, with whom she had a brief, torrid romance — while playing, it must be said, his older sister,” penned Jim Nelson, who served as a writer’s assistant on “Ferris Bueller.” Nelson went on to become the editor-in-chief of GQ and wrote a tell-all piece about his time as a Hollywood assistant, describing himself as the “Taker of All Notes” and the “Keeper of Comedy” on the production. While he dished a ton regarding who treated him badly at the time, Aniston was not to be in that mix. “She was lovely, kept to herself on the set, smoldering a bit like her outraged character, 17-year-old Jeannie Bueller,” he said of the budding actor.
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She worked with Tate Donovan on ‘Friends’ during their real-life break-up
While Jennifer Aniston has nothing but fond memories about working with ex-husband Brad Pitt on “Friends,” unfortunately the same can’t be said for one of her other real-life loves: Tate Donovan. It all came down to timing. Many assume that the “Murder Mystery” star and “The O.C.” alum dated as a result of his guest role on the sitcom, but his gig on the hit show actually coincided with their breakup. “The people that know that we dated think that we met on “Friends.” But in fact, we had dated for two years before then, and it was over by the time we were on “Friends” together,” the “Argo” star revealed to Us Weekly.
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Donovan debuted on the show with the episode, “The One With Rachel’s Crush,” playing the role of Joshua Burgin, otherwise known as (you guessed it) Rachel’s crush. “I was just happy to be on the team. The only bummer was Jennifer and I were breaking up at the time. And so 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,” the “Shooter” star explained.
In fact, the actors decided that it would be in everyone’s best interest if Rachel’s romance with Joshua didn’t continue. “It was just six episodes. I mean, only because we were breaking up. We were like, ‘Hey, can we not keep doing this? ‘Cause this is really painful and tough,'” Donovan admitted.
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Vince Vaughn brought her ‘back to life’ after splitting with Brad Pitt
While Jennifer Aniston and Brad Pitt’s relationship stands in a different place years after their divorce, there was a time when things between the couple were contentious at best, and hostile at worst. Rumors that Pitt cheated on Aniston with Angelia Jolie after doing a film together ran rampant, while the media toted the narrative that the “Friends” alum’s refusal to have children was what put the final nail in the coffin of the popular couple’s union. Regardless of who was to blame, it was a difficult time for both parties. Therefore, when Aniston sparked with Vince Vaughn on the set of “The Break-Up” in 2005, it’s no wonder she was looking for some happiness in her life. Sadly, the new couple was soon headed for their own real-life break-up, splitting in December of the following year.
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“I call Vince my defibrillator,” she revealed to Vogue back in 2008, a few years after the pair called it quits. “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.”
While neither party was forthcoming about the reason for the split, Vaughn did eventually admit the attention was a little too much for him. “You know, she’s great. For me personally — and I think most well-known actors who are together feel this way — I never enjoyed the paparazzi side of it,” the “Wedding Crashers” star said to Playboy in February 2015 (via People).
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Her second husband Justin Theroux was a co-star
While the truth about many of Jennifer Aniston’s famous exes continues to be a point of speculation, one name that’s frequently brought up is that of her second husband Justin Theroux. Although the pair were introduced years before on the set of “Tropic Thunder” when Aniston was there to visit with Ben Stiller in 2007, they didn’t pursue a romantic relationship until they co-starred in “Wanderlust” in 2010. In less than a year they were living together, and they wed in 2015 at a secret event that guests arrived to expecting to celebrate Theroux’s 43rd birthday.
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The relationship didn’t last, with the couple announcing their split after only two years of marriage. “In an effort to reduce any further speculation, we have decided to announce our separation. This decision was mutual and lovingly made at the end of last year. We are two best friends who have decided to part ways as a couple, but look forward to continuing our cherished friendship,” they revealed in a joint statement (via People).
The reason why Aniston and Theroux really divorced has been puzzled over due to their seemingly friendly demeanor, and it was reported that long-distance and separate interests may have been to blame, but Theroux himself claimed that wasn’t the case. “That’s a narrative that is not true, for the most part,” he told Esquire in April 2021. “People create narratives that make themselves feel better or simplify things for them. That whole ‘This person likes rock ‘n’ roll, that person likes jazz. Of course!’ That’s just not the case. It’s an oversimplification.” The “Mulholland Drive” star insisted the truth wasn’t anything dramatic. “Like it or not, we didn’t have that dramatic split, and we love each other,” he said. “She’s a hilarious person. It would be a loss if we weren’t in contact, for me personally. And I’d like to think the same for her.”
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