What Jennifer Aniston's Exes Have Said About Her

There's an endless obsession with celebrity relationships, but there's one certain A-lister whose love life is always in question. That celeb is none other than Jennifer Aniston. Is it because fans hope for reconciliation between Aniston and her ex-husband Brad Pitt? We've seen it happen with Jennifer Lopez and Ben Affleck. Or, are we dreaming of a real-life romance between Jen and David Schwimmer, aka Rachel Green and Ross Gellar from "Friends?" 

Aniston has reportedly been single since her separation from Justin Theroux in 2018. Despite this, "The Morning Show" star hasn't given up on love. Though she told Allure in 2022 that she isn't interested in remarrying, she did share, "I'd love a relationship. Who knows? There are moments I want to just crawl up in a ball and say, 'I need support.' It would be wonderful to come home and fall into somebody's arms and say, 'That was a tough day.'"

But, whatever the reason for our unhealthy obsession with Aniston's love life, it's really not any of our business — though fans are rooting for her to find "the one." However, we can take a deep dive into her past relationships and think back to what her exes have had to say about her, including her two ex-husbands and the men who had brief romances with Aniston.

Four years before Jennifer Aniston landed the coveted role of Rachel Green on "Friends," she starred in the 1990 television adaptation of the popular film "Ferris Bueller's Day Off." Actor Charlie Schlatter starred as Ferris, while Aniston portrayed his older sister, Jeannie. Titled "Ferris Bueller," the show was canceled after one season after receiving poor ratings. 

It wasn't until 2014 that fans learned of a short-lived romance between Aniston and Schlatter. GQ writer Jim Nelson, who worked as a writer's assistant, shared, "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." However, neither Aniston nor Schlatter ever confirmed or denied having a relationship. 

In 2019, Aniston was presented with a photo of the cast of "Ferris Bueller" during a red-carpet interview with Access Hollywood. When asked if she'd be up for a reunion, the actor said, "That would be a really, absolute no. I don't even think half of those actors are even still in the business. Some of them have gone to do other really wonderful, noble things. Hard no." 

During an interview with Rolling Stone in 1999, Jennifer Aniston shared that her "first real, mature relationship" was with actor Daniel McDonald, with whom she dated from 1990 to 1995. McDonald guest-starred in several television shows, including "Sex and the City" and "Law & Order." His big break came when he starred in the Broadway show "Steel Pier," receiving a Tony Award nomination for his role. 

In a 2015 interview with The New York Times, Aniston hinted that McDonald may have been the one that got away. "He was my first love — five years we were together. He would have been the one. But I was 25, and I was stupid. He must have sent me to Justin [Theroux] to make up for it all," Aniston said, referring to her then-fiance. 

McDonald died in 2007 from brain cancer at the age of 46. At the time of his death, he was married to Mujah Maraini-Melehi, with whom he shared two children. McDonald's widowed wife was extremely upset with the media handling Aniston's interview with The New York Times. She expressed her frustrations in a lengthy Facebook post: "My heart aches to see our tragedy of losing Daniel to serve the media's hunger for sensationalism ... It pains me to read the headlines that allude to her losing him tragically when she was not present during his long and difficult illness ... I know how much Daniel cared about her, and how protective he was of her. That was part of what I loved about him."

It's unclear how long Jennifer Aniston dated Counting Crows' lead singer Adam Duritz, but their short-lived relationship occurred sometime in 1995. Speaking with ET in 2021, Duritz recalled first meeting Aniston at the famous Los Angeles music venue The Viper Room. In addition, the "Mr. Jones" singer revealed how he and Aniston were awkwardly set up. 

"A bunch of my friends lied to me and told me she had a crush on me. Those same friends lied to her and told her I had a crush on her. I honestly had no idea who she was, I had been on the road during 'Friends.' I had never seen it, I don't think," Duritz said. He added, "It didn't last very long, but she's a nice girl." According to Us Weekly, the lead singer even mentioned that he and Aniston didn't even make it to third base when he said, "We never even slept together." 

According to ET, Duritz went on to date Aniston's "Friends" co-star Courteney Cox in 1997. In an interview with Men's Health in 2014, he simply shared, "They were nice girls and I went out with them and that was that."

"The O.C." star Tate Donovan was set up with Aniston by mutual friends in 1995 after he had previously dated Sandra Bullock. "He's so real, so honest, so funny, so kind and considerate. He's all these things meshed into one perfect guy," Aniston gushed to People in 1997. In that same interview, Donovan even talked about the possibility of marriage, stating, "I definitely want to get married; she definitely wants to get married. There are no proposals or anything, not yet, but we definitely think about it." Though there are conflicting reports on whether Donovan popped the question, the couple split in 1998.

That same year, Donovan landed a recurring role on "Friends." Um, awkward much? For six episodes, Donovan starred as Rachel Green's crush, Joshua Burgin. He recalled to Us Weekly how difficult it was to work alongside his ex. "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," he shared.

Looking back, Donovan added that though the entire "Friends" cast was great, he admitted feeling like he was "sort of dying inside" throughout his time working on the show. In 2005, Donovan married Corinne Kingsbury, but the couple divorced in 2008.

The late '90s gave us Hollywood's most talked about couple: Jennifer Aniston and Brad Pitt. The duo began dating in 1998 and tied the knot two years later. Pitt even joined his wife on "Friends," starring in a Thanksgiving episode as a character who despised Rachel Green.

Just as "Friends" was wrapping up in 2004, Aniston appeared to be ready to start a family with Pitt when she told The Guardian, "It's time. It's time. You know, I think you can work with a baby, I think you can work pregnant, I think you can do it all." However, the power couple shocked the world with their split in early 2005. Rumors swirled that Pitt strayed and cheated on his wife with his "Mr. & Mrs. Smith" co-star Angelina Jolie, with whom he would end up dating shortly after his divorce. The two eventually married in 2014 but filed for divorce two years later. 

In 2007, Pitt told V magazine (via People) that he and Aniston "still maintain a deep friendship" despite their separation. However, his 2011 interview with Parade had fans questioning his marriage to Aniston when he revealed that he "wasn't living an interesting life." The "Moneyball" actor had to clarify his statements: "The point I was trying to make is not that Jen was dull, but that I was dull to myself – and that I am responsible for" (via Reuters). In 2020, all seemed to be well between the exes when they were spotted reuniting at the SAG Awards. Sadly, it didn't mean these two stars were rekindling their romance.

It was Vince Vaughn to the rescue after Jennifer Aniston and Brad Pitt's historic split. The two actors began a relationship in the summer of 2005 while filming their comedy "The Break-Up." At the time, Vaughn told People, "She's awesome. She has just a wonderful warmth and likability about her." However, by the end of 2006, Aniston and Vaughn called it quits but remained on good terms. 

Since their split, the pair would continue to say nothing but good things about one another. In 2008, Aniston reflected on her short-lived relationship with Vaughn, telling 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."

In an interview with Playboy in 2015 (via Daily Mail), Vaughn revealed how overwhelming it was to deal with the media covering their romance. "For me personally — and I think most well-known actors who are together feel this way — I never enjoyed the paparazzi side of it," Vaughn shared. He added, "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. I think lying low and not talking about it put me in a good position later, because I just wasn't part of anything."

In 2010, Vaughn married Kyla Weber, and they welcomed two children. 

And then there was John Mayer. Jennifer Aniston and the "Your Body Is a Wonderland" singer dated on and off for about a year after meeting at an Oscars after-party in 2008. They split in August and Mayer held an impromptu meeting outside his New York gym to discuss their initial break up: "There's no lying, there's no cheating, there's no nothing ... People are different, people have different chemistry." However, the former couple gave it another go, with Aniston bringing Mayer along as her date to the 2009 Oscars. They split shortly after. 

In an interview with Rolling Stone in 2010, Mayer shared that the split was one of the hardest times he's ever been through. "I have this weird feeling, a pride thing, for the people I've had relationships with ... What would I be saying to Jen, who I think is f****** fantastic, if I said to her, 'I don't dislike you. In fact, I like you extremely well. But I have to back out of this because it doesn't arc over the horizon. This is not where I see myself for the rest of my life, this is not my ideal destiny,'" he said.

That same year, Mayer's widely controversial Playboy interview came out. In it, the singer confessed to still loving Aniston, however, he appeared to take a dig at their age difference: "I'll always be sorry that it didn't last. In some ways I wish I could be with her. But I can't change the fact that I need to be 32." Despite this, the singer attended Aniston's 50th birthday celebration in 2019. 

Fans of Jennifer Aniston were happy to see the actor find love again with Justin Theroux. Though they first met on the set of "Tropic Thunder" in 2007, they didn't strike up a romance until 2011, when they worked together in "Wanderlust." It wasn't long until Theroux proposed to the star in 2012, and the two wed in a top-secret ceremony at their California home in 2015.

It was extremely shocking to hear the news of Aniston and Theroux's split in February 2018. However, like many of her previous relationships, the "Horrible Bosses" star and her ex remained friendly. Theroux first spoke out about their split with The New York Times, sharing, "The good news is that was probably the most — I'm choosing my words really carefully – it was kind of the most gentle separation, in that there was no animosity." In addition, the actor did share that though there was no hostility between him and Aniston, the separation "was heartbreaking, only in the sense that the friendship would not be the same, as far as just the day to day."

With time to heal, it appeared that their friendship had gotten better. In 2021, Theroux told Esquire that the twosome Facetime on occasion, adding, "I'm sincere when I say that I cherish our friendship ... It would be a loss if we weren't in contact, for me personally. And I'd like to think the same for her."