With over three decades in Hollywood, Jennifer Aniston has had her share of high-profile romances.

 Her early aughts marriage to Brad Pitt captivated public attention, so much so that a backstage run-in between the pair in 2020 dominated headlines 15 years after their divorce.

More recently, Aniston spent nearly a decade with The Leftovers’ Justin Theroux. And despite parting ways, the exes remain in each other’s lives, with Theroux having told The Times that Aniston is still “very dear” to him in a 2023 interview.

Since then, Aniston has reportedly been enjoying the private pleasures of a low-key dating life, with no publicly known relationships thus far. Before Aniston decided to take her romances out of the spotlight, she had some prolific partners dating back to her days winning everyone’s hearts as Rachel on Friends. Ahead, a complete full timeline of The Morning Show’s former flames.

Daniel McDonald

Aniston credits her “first love” to actor Daniel McDonald, who Aniston dated when she was 25. They broke up “just before Friends,” Aniston revealed in a 1999 interview with Rolling Stone. 26 years later, the actress reflected on the relationship for The New York Times, candidly admitting that “He would have been the one. ​​But I was 25 and stupid. He must have sent me Justin [Theroux] to make up for it all.”

Tragically, the Tony nominee passed away in 2007 at the age of 46 after a battle with brain cancer.

Charlie Schlatter

Jennifer Aniston and Charlie Schlatter at an NBC party in 1990.Barry King/Getty Images

Before Aniston had reached the level of super-star celeb, she was on a ‘90s TV spinoff of John Hughes’s Ferris Bueller’s Day Off. In NBC’s short-lived Ferris Bueller, actor Charlie Schlatter played the titular role, while Aniston played his sister, Jeannie. Off screen, things between the two were reportedly romantic.

This dating gossip was revealed in an essay penned by former GQ editor-in-chief Jim Nelson, who had once worked as a writer’s assistant on sitcoms during the ‘90s. He was not shy speaking about Schlatter and Aniston’s “brief, torrid love affair.”

Adam Duritz

Jennifer Aniston and musician Adam Duritz attend the “Mr. Jenkins Soiree” in Los Angeles on September 29, 1995.Ron Davis/Getty Images

When Adam Duritz, lead singer of rock band Counting Crows, met Jennifer Aniston, he “had no idea” who she was. “I had been on the road during all of Friends,” he revealed in an interview for VICE TV’s Dark Side of the ’90s. But at the infamous LA club The Viper Room, Duritz’s friends goaded the two into talking. “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.”

The two subsequently dated for a short spell in 1995, when one of their only public photos together was captured at the Mr. Jenkins Soiree in Los Angeles. But Duritz only has good things to say about his ex looking back: “She was really nice, really funny, really pretty, those were pretty good requirements for me and also she liked me. It didn’t last very long, but she’s a nice girl.”

Tate Donovan

Jennifer Aniston and Tate Donovan at the New York premiere of “Picture Perfect” in 1997.Kevin.Mazur/Getty Images

On Friends, actor Tate Donovan played Joshua, Rachel’s love interest for six episodes during Season 4. But off the show, Donovan and Aniston were quietly ending their real-life relationship.

The two had met before Donovan joined the sitcom and they dated for more than two years, even moving in together, as Donovan explained to The Independent in 2024. But when Donovan was cast on Friends as a fling for Rachel, their relationship was well into petering out. “It’s like going to class when you’re in high school and you’ve broken up with the girl who you sat next to…” Donovan said in that same interview. Although rumors had circulated that their disparate successes had contributed to the breakup, Aniston shot down those rumors in a 1999 interview with Rolling Stone. “Tate’s and my breakup had nothing to do with ego battles, wanting babies, not wanting marriage—all that stuff. None of it was accurate,” she clarified.

In a 2020 interview between Aniston and Sandra Bullock for Interview Magazine, the two exes of Donovan’s lightheartedly noted their old boyfriend’s good taste in women and how it led to their eventual friendship.

Brad Pitt

Brad Pitt and Jennifer Aniston at the 1999 Emmys.Jim Smeal/Getty Images

Aniston’s short marriage to Brad Pitt remains one of Hollywood’s most famous couplings, and they met in the most Hollywood way possible: through their managers. Introduced to one another in 1994, the two wouldn’t actually go on to become romantically entangled until a few years later. Once Aniston had broken off from Tate Donovan and Pitt was no longer engaged to Gwyneth Paltrow, this time, it stuck.

The couple made their red carpet debut at the 1999 Emmys, and a very public engagement announcement followed suit a month later: Aniston showed off her diamond-and-platinum engagement ring on stage at a Sting concert at New York City’s Beacon Theater. In July of the following year, the pair were officially husband and wife. Surrounded by 200 of their friends and family in Malibu, the decadent ceremony cost an estimated $1 million, according to Marie Claire. During their vows, Pitt cheekily promised to “split the difference on the thermostat,” while Aniston pledged she would always make his “favorite banana milk shake,” according to People.

Aniston and Pitt enjoyed marital bliss for the next few years, and Pitt guested on a memorable Thanksgiving episode of Friends titled “The One with the Rumor.” In 2021, Aniston spoke fondly of Pitt’s performance for Access, saying that he was “wonderful.” They even co-founded a production company together: Plan B Entertainment, alongside producer Brad Grey.

Brad Pitt and Jennifer Aniston at the Warner Bros. Premiere of “Troy” on May 10, 2004.Sylvain Gaboury/Getty Images

Then, in a 2003 interview with W magazine, Aniston bristled when the interviewer called Pitt the love of Aniston’s life. “I mean, I don’t know, I’ve never been someone who says, ‘He’s the love of my life.’ He’s certainly a big love in my life…” she said. Nevertheless, in 2004 Aniston spoke of her eagerness to start a family with Pitt, telling The Guardian “it’s time.”

But less than a year after that interview in The Guardian, the couple had given their joint separation statement exclusively to PEOPLE. “We would like to announce that after seven years together we have decided to formally separate.” Nine months later, their divorce was finalized.

Brad Pitt and Jennifer Aniston at the World Premiere of the movie “Troy” on May 13, 2004 in Cannes, France.Evan Agostini/Getty Images

Though Pitt’s then-blossoming relationship with Angelina Jolie was difficult to watch for Aniston, the two stars have kept good on their promise to stay in one another’s lives. Pitt attended Aniston’s 50th birthday party in Los Angeles and then reunited with her warmly at the 2020 SAG awards, where both actors took home honors. They even participated in a virtual table read of Fast Times at Ridgemont High amidst COVID lockdowns. In 2021, Aniston told Howard Stern that the two exes are “buddies.”

Vince Vaughn

Jennifer Aniston and Vince Vaughn at the French open in 2006.Stephane Cardinale – Corbis/Getty Images

Aniston’s first relationship post-Pitt was with her co-star Vince Vaughn, while the two of them filmed the aptly-titled The Break-Up. Although the relationship lasted less than a year, Aniston credited Vaughn for reviving her after her extremely public divorce. Reflecting on their time together in a 2008 interview with Vogue, Aniston referred to Vaughn as her “defibrillator.” “He literally brought me back to life,” she said.

After Aniston took a trip to London in 2006 to visit Vaughn on the set of Fred Claus, the couple released a joint statement saying that they had decided to call it quits. Like Aniston, Vaughn similarly had good things to say about Aniston, and in a 2015 interview with Playboy Magazine, he said that she’s “great.”

However, he also revealed that he never enjoyed the media scrutiny that followed her. “For me personally — and I think most well-known actors who are together feel this way — I never enjoyed the paparazzi side of it,” he admitted. “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.”

John Mayer

Jennifer Aniston and John Mayer at the 2009 Vanity Fair Oscar Party.Jon Kopaloff/Getty Images

Aniston’s fleeting fling with John Mayer took the world by storm back in 2008, not long after she had split from Vince Vaughn. The two stars met at an Oscar party in February that year and quickly began dating, even though Aniston admitted that she “barely knew his music” in an interview with Vogue.

The pair vacationed to Miami, Mexico, and Europe together, but after only a few months of dating they briefly parted ways. Mayer had said to inquisitive paparazzi at the time, “I ended a relationship to be alone, because I don’t want to waste somebody’s time if something’s not right.” Yet a few weeks later, the couple was back on, spotted together at Mayer’s birthday in Los Angeles and at a dinner in New York City.

A year out from their first meeting, they were still thick as thieves at the 2009 Oscar party, but things fizzled out permanently shortly after with a source at the time citing “disagreements.” In 2010, Mayer confessed to Rolling Stone that he’s “Never really gotten over it. It was one of the worst times of my life.”

Justin Theroux

Jennifer Aniston and Justin Theroux attend the 2017 Vanity Fair Oscar Party.JB Lacroix/Getty Images

Justin Theroux was Aniston’s longest-lasting love, and the two have held onto their friendship since their divorce. They first met via their mutual friend, Ben Stiller, on the set of Tropic Thunder, which Stiller directed and Theroux co-wrote. Theroux made quite the impression on Aniston: “I started to sweat just looking at him,” she told Popsugar in 2012.

However, they didn’t begin dating just yet. They reconnected in 2010, on the set of their film Wanderlust, and the following year, the two were regularly spotted together out and about, double-dating with friends, and even wearing matching rings. Aniston threw him a kiss while he was front row at her Hand and Footprint Ceremony in LA.

By 2012, the couple were speaking more openly about their relationship. In the March issue of InStyle, Aniston opened up about her “joyful” and “peaceful” relationship with Theroux. For his part, Theroux told New York Magazine about adopting their new puppy, but was keen to keep his private life private. “I understand the curiosity, but other than saying I am happy, I am not going to indulge it,” he explained candidly. “That’s building your own torture device.”

Justin Theroux and Jennifer Aniston at the Oscars on February 24, 2013 .Kevork Djansezian/Getty Images

Later that same year, at his 41st birthday dinner, Theroux popped the question. The couple tied the knot two years later on August 5, 2015, in a private, backyard ceremony in Bel-Air, California. “It’s so much more special when it’s just your closest friends and family and it’s lovely,” Theroux told Entertainment Tonight.

For the next couple years, things seemed to be going smoothly for the two stars, while Aniston dodged incessant pregnancy rumors and the two even redesigned their home. But in February 2018, Theroux and Aniston shocked the world with the announcement that they were parting ways. In a joint statement, they announced that “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.”

Seven months later, Theroux spoke about his “heartbreaking” divorce from Aniston in an interview with The New York Times. Still, there was “no animosity,” he clarified. “It’s more like, it’s amicable. It’s boring, but, you know, we respected each other enough that it was as painless as it could be.” In 2022 Aniston would go on to disclose her struggles with infertility to Allure: “All the years and years and years of speculation… It was really hard. I was going through IVF, drinking Chinese teas, you name it. I was throwing everything at it.”

Since their split, Theroux and Aniston have continued to maintain a happy bond. In 2024 Theroux revealed to The Times that Aniston is still “very dear” to him. Aniston was even reportedly one of the “first to congratulate” her ex on his recent nuptials to actress Nicole Brydon Bloom earlier.