In September 2021, the “Morning Show” star stated she was looking for love again. But she insisted that she would not use dating apps to find it. No one of significance has crossed my path, but I believe the time has come. In an interview with SiriusXM, she said, “I think I’m ready to share myself with another. Aniston believes there is someone out there for her despite two public divorces (one of which involved a long-rumored cheating scandal) and several relationships with high-profile men. And, while the “Friends” alum was deni rumors that she and former co-star David Schwimmer were ever romantically involved. She does have a romantic history: Aniston’s flings, boyfriends, husbands.
Aniston had a brief romance with teen heartthrob Charlie Schlatter in the 1990s. The two met on the 1990 sitcom “Ferris Bueller,” based on the 1986 film “Ferris Bueller’s Day Off.” Their show only lasted one season, and their relationship didn’t last much longer. Schlatter married Colleen Gunderson in May 1994, and the couple has three children. In April 2014, GQ editor-in-chief Jim Nelson revealed that Aniston and Schlatter had a “brief, torrid romance—having to play, it must be said, his older sister.”
Aniston’s first real relationship was with the late Daniel McDonald. Aniston and the actor dated for five years in the early 2000s. Aniston later refers to the actor as “the one who got away. She told “Entertainment Tonight” in January 2015 that “he was her first love—we were together for five years,” she told “Entertainment Tonight” in January 2015.
Jon Stewart appears to believe he dated Aniston in the early 1990s, though she did not. I asked you out, & it was lovely,” the actor recalled, asking the actress out in August 2010, “and it was lovely.” I understand you are bringing a large group of your friends. And I did think, “She’s so excited to be on a date with me [that] she wants me to meet her entourage.” If I recall correctly, wasn’t it sort of like, “Hey, a group of us are going out.
The “Dumplin” star had a brief romance with Adam Duritz in 1995, but things did not appear to get too hot and sweaty between the two. The Counting Crows frontman admitted that he had no idea who Aniston was when they met or that their relationship began because friends duped him.
Aniston began dating actor Tate Donovan in 1995, but the couple split up two years later. In five episodes, Donovan famously played Rachel Green, Aniston’s “Friends” character, even though the pair had already moved to Splitsville, Virginia, in real life. Fortunately, while dating Donovan, Aniston formed a friendship with him, revealing that he was the one who introduced her to gal pal Sandra Bullock.
Aniston was rumored to have dated Paul Rudd for several years, but the timeline is unknown. The couple appeared in love as they co-starred in their 1998 film “The Object of My Affection.”
In the late 1990s, it appeared that Aniston had finally found happiness with none other than Brad Pitt. In true Hollywood fashion, the couple met in 1994, but it wasn’t until 1998 that they went on their first date, set up by their agents. While they attempted to keep their romance private, the couple quickly became tabloid favorites, with the entire country watching their love blossom.
A hot commodity like Aniston doesn’t stay single for long, so it’s no surprise that she moved on from her messy split with Pitt to Vince Vaughn. The couple only dated for a year, ending in November 2006, but Aniston seemed thankful for their brief romance.
Many fans have forgotten about Aniston’s steamy romance with John Mayer. The couple met at an Oscars party in February 2008 and dated until March 2010. “We care about one another. It’s hilarious when you reach a point in a relationship where you both realize. We might need to do something else,” but you still adore each other. “It’s hurtful,” she told Vogue in December 2008, during one of their splits.
When her second marriage to Justin Theroux didn’t work out, Aniston found herself in the throes of heartbreak once more. The stars met on the set of the 2008 film “Tropic Thunder, ” co-written by Theroux, and starred one of Aniston’s close friends, Ben Stiller. Years later, they collaborated for the first time, co-starring in the 2012 film “Wanderlust,” which also starred her ex, Rudd.