Entertainment Movies Jennifer Aniston's Dating History: From Brad Pitt to Justin Theroux After splitting from Brad Pitt in 2005, Jennifer Aniston dated John Mayer and later married Justin Theroux By Jacqueline Weiss Jacqueline Weiss Twitter Jacqueline Weiss is a contributing writer at PEOPLE. She has been working at PEOPLE since 2022. Her work has previously appeared in Food & Wine, Insider and Apartment Therapy. People Editorial Guidelines Published on March 30, 2023 01:21 PM Share Tweet Pin Email Photo: Evan Agostini/Getty ; Anthony Harvey/Getty Jennifer Aniston has plenty of gratitude for her past relationships. In 2019, she opened up about her marriages with exes Brad Pitt and Justin Theroux. "My marriages, they've been very successful, in [my] personal opinion," she said. "And when they came to an end, it was a choice that was made because we chose to be happy, and sometimes happiness doesn't exist within that arrangement anymore." Aniston continued, "Sure, there were bumps, and not every moment felt fantastic, obviously, but at the end of it, this is our one life and I would not stay in a situation out of fear. Fear of being alone. Fear of not being able to survive. To stay in a marriage based on fear feels like you're doing your one life a disservice." In addition to her nuptials, Aniston has had several other high-profile relationships over the years, but she's looking for one outside the industry. "That'd be nice," she told PEOPLE in 2021. Here's a look back at Jennifer Aniston's dating history. Charlie Schlatter Ron Galella, Ltd./Ron Galella Collection In 1990, the young actress starred on NBC's Ferris Bueller, a sitcom inspired by Ferris Bueller's Day Off. The show ran for a total of 13 episodes. Aniston, who played Ferris' sister Jeannie, met leading man Charlie Schlatter on set. In 2014, GQ's Editor-in-Chief Jim Nelson wrote about his time as a Hollywood assistant. Nelson revealed that the on-screen siblings had a "brief" off-screen relationship, which he witnessed while working as a writer's assistant on Ferris Bueller. "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," he wrote. Daniel McDonald Reisig & Taylor/NBCU Photo Bank/NBCUniversal ; Walter McBride/Corbis From 1990 until 1995, Aniston dated actor Daniel McDonald, who died from brain cancer in February 2007, according to Playbill. "He was my first love — five years we were together," she told The New York Times in 2015. "He would have been the one. But I was 25, and I was stupid. He must have sent me Justin [Theroux] to make up for it all." Adam Duritz Ron Davis/Getty In 1995, Aniston briefly dated Counting Crows frontman Adam Duritz after meeting at The Viper Room. "A bunch of my friends lied to me and told me she had a crush on me," Duritz recalled in 2021. "And those same friends lied to her and told her I had a crush on her. I honestly had no idea who she was." Duritz continued, "She was nice, really funny, really pretty. Those are pretty good requirements for me and also she liked me. It didn't last very long, but she's a nice girl." Tate Donovan Ron Galella/Ron Galella Collection via Getty In 1995, the Picture Perfect actress started dating actor Tate Donovan, who had just ended his relationship with Sandra Bullock. In 1998, he was cast as Rachel Green's love interest on Friends — just as their off-screen relationship ended. "He seems to have a type," Aniston later joked with Bullock in 2020, discussing their former mutual boyfriend. A few years after he and Aniston broke up, Donovan went on to marry Corinne Kingsbury, though they divorced in 2008. Brad Pitt Richard Corkery/NY Daily News Archive Aniston and Brad Pitt's managers introduced the pair in 1994, but it wasn't until 1998 that they went on their first date. The following year, they made their red carpet debut at the 51st Emmy Awards. They announced their engagement in November at a Sting concert, where they showed off Aniston's ring on stage. On July 29, 2000, Aniston and Pitt got married in front of 200 guests at a private estate in Malibu, California, overlooking the Pacific Ocean. The night included a live performance by Melissa Etheridge, 50,000 flowers and a fireworks show. Pitt made a guest appearance on Friends' Thanksgiving episode in 2001, playing a character who hated Aniston's Rachel Green. As the show neared its end, the actress hinted that she and Pitt may have been ready to have a child together. "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 all of it," she told The Guardian in February 2004. Around the same time, rumors began to swirl about Pitt and his Mr. & Mrs. Smith costar, Angelina Jolie, who later shared that they became close friends on set. In January 2005, Aniston and Pitt announced that they were separating after almost five years of marriage. "We would like to announce that after seven years together we have decided to formally separate," they told PEOPLE in a statement. "For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media." The statement continued, "This decision is the result of much thoughtful consideration. We happily remain committed and caring friends with great love and admiration for one another. We ask in advance for your kindness and sensitivity in the coming months." Aniston officially filed for divorce in March, and the split was finalized in October. In 2020, the exes were spotted chatting at the 2020 Screen Actors Guild Awards, but they have maintained they are just friends. Vince Vaughn JACK GUEZ/AFP In summer 2005, Aniston began dating her costar Vince Vaughn while filming The Break-Up in Chicago. "She's awesome," Vaughn told PEOPLE in June. "She has just a wonderful warmth and likability about her." By December 2006, however, Aniston and Vaughn had called it quits. "After Jennifer's trip to London several weeks ago, Jennifer and Vince mutually agreed to end their relationship but continue to be good friends today," their reps told PEOPLE. Aniston stayed silent about the split until 2008, when she looked back fondly on their short time together. "I call Vince my defibrillator," she 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'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." John Mayer Kevin Mazur/VF/WireImage After meeting at an Oscars party in early 2008, Aniston and John Mayer dated on-and-off for about a year. By August, things fizzled out for the couple. "I ended a relationship to be alone, because I don't want to waste somebody's time if something's not right," Mayer told reporters. The couple briefly reunited in February 2009 and attended the Oscars together, where Aniston was a presenter. However, they ended their relationship again shortly after. "They had some disagreements and decided to not continue to see each other," a source told PEOPLE at the time. "Jen is moving on with her life like she always does. She seems happy." In 2010, the "Gravity" singer said of their split, "I've never really gotten over it. It was one of the worst times of my life." Justin Theroux Dimitrios Kambouris/Getty In 2007, Aniston visited the set of her friend and former costar Ben Stiller's new movie, Tropic Thunder, where she met Justin Theroux. Aniston and Theroux reconnected in 2010 on the set of Wanderlust, and by August 2011, they had moved in together. On Aug. 5, 2015, the couple said "I do" in an intimate ceremony at their Bel Air, California home. They tricked friends and family by telling them they were attending Theroux's 43rd birthday party. "Part of the fun of planning a wedding is telling people and we had to keep it under wraps," the actor said. Aniston and Theroux made their final public appearance as a couple in July 2017 at Jason Bateman's Hollywood Walk of Fame star ceremony. Days after Aniston's birthday in 2018, the couple announced that they had separated after two-and-a-half years of marriage. "In an effort to reduce any further speculation, we have decided to announce our separation," the couple said in a statement. "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 continued, "Normally we would do this privately, but given that the gossip industry cannot resist an opportunity to speculate and invent, we wanted to convey the truth directly. ... Above all, we are determined to maintain the deep respect and love that we have for one another." Aniston and Theroux have remained supportive of each other in the years following their divorce, regularly keeping in touch and even celebrating each other's birthdays.