People have been interested in Jennifer Aniston’s romantic life for many years. Her high-profile marriage to Brad Pitt, which ended in 2005, was a particular focus of the media. Aniston was honest about the pain of their breakup and how the rumors about Pitt’s new relationship with Angelina Jolie affected her.
Later, she fell in love again with actor and writer Justin Theroux. Their small wedding was a surprise to their guests, but the couple said that they had felt “already married” for a while. But, after two years of being apart, they decided to end their relationship.
Even though they are no longer married, Aniston and Theroux are still close friends, and they continue to make each other laugh and bring each other joy. Aniston is still optimistic about her love life, and she has said that it’s important to choose happiness, even if it means ending a relationship.
Jennifer Aniston’s Dating History:
Charlie Schlatter
After working together on the short-lived 1990 TV remake of the John Hughes movie Ferris Bueller’s Day Off, there were rumors that Aniston and Schlatter were dating.
Daniel McDonald
During an interview with The New York Times in January 2015, the Dumplin’ actress called McDonald her “first love” and said, “He was going to be The One.” But I was only 25 and foolish.”
Before they broke up, Aniston and McDonald, who died in 2007 from brain cancer, dated for five years.
Jon Stewart
Over 20 years ago, the comedian and the actress went on a date. In August of 2010, Stewart reminded Aniston on The Daily Show, “I asked you out and it was nice.” I remember you have so many of your friends around you. She’s so excited to go out with me, I remember thinking, and she wants me to meet her friends.
The star of The Office Christmas Party disagreed, saying, “If I remember right, it was more like, “Hey, a few of us are going out. Do you want to come?”
Adam Duritz
In 1995, Aniston and the frontman of the band Counting Crows had a short relationship. After they broke up, Duritz briefly moved on with Courteney Cox, who was Aniston’s co-star on Friends and best friend in real life. For her part, the Scream star has been with Johnny McDaid since 2013.
Tate Donovan
Donovan was happy to be offered a six-episode arc on Friends in 1998, but it was hard for him to play the part because he and Aniston were going through a divorce at the same time.
“I was simply glad to join the team. The only disappointment was that Jennifer and I were breaking up at the time, the Argo actor told Us in September 2018.
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It was hard to act like we were just getting to know each other and falling in love or becoming interested in each other while planning to break up. That was really tough.
Paul Rudd
The Object of My Love Co-stars kept their rumored romance a secret for many years, but Aniston eventually said, “We were together when we were, like, 12.”
Also, the actors were in The Newton Boys in 1998, Wanderlust in 2012, and Friends from 2002 to 2004.
Brad Pitt
In 1998, Aniston and the Oscar winner started dating. They finally got married in 2000. But when they broke up in 2005, it surprised everyone. Pitt was being accused of having an extramarital affair with his Mr. & Mrs. Smith co-star, who he had started dating soon after his breakup with the Mother’s Day actress.
Pitt and Jolie, who had been married for two years and had six children together, got a divorce in 2016. In 2019, the divorce was finalized.
Vaughn
The Cake actress moved on from Pitt with Vaughn from Wedding Crashers, but rumors about the relationship led to its end in December 2006. In February 2015, the True Detective star told Playboy magazine, “You know, she’s great.”
Spending time with someone you like and like is not the same thing as liking them; everything was fine. Yet, I spent most of that time figuring out how to avoid drawing attention.”
He was great for the time we were together, but Aniston couldn’t look back on the relationship with fondness. She told Vogue shortly after the breakup, “He was lovely and fun.” I also needed that. And it sort of finished its journey.
Paul Sculfor
In 2007, the British model dated Aniston for a short time, but things never got serious. At the time, an insider told us that there was no drama. They “hang out and have a few dinners.”
From April 2008 to March 2009, the singer and actress had an on-and-off relationship.
After their last breakup, the “Gravity” singer said on CBS’s “Sunday Morning” that he was “just a jerk” while they were dating.
In a later interview with Playboy, he said, “That pearl of possibility that lives in your heart when you meet someone you want to know more about is so different from everything else that you have to go after it.
I wouldn’t do it either, guy. I would have been better off if it had worked out, after all. When I get home, I’ll have what I’ve always wanted, I’d say as I sit here.
Bradley Cooper
After working together in He’s Just Not That Into You, Cooper and Aniston had a short romance that summer. They never had a long-term relationship, but they were always friendly.
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Gerard Butler
After working together in The Bounty Hunter, Butler, and Aniston became the subject of dating rumors. Later, the Friends alum and the Olympus Have Fallen star told Us that they had laughed off the dating rumors. He said, “It’s a little bit silly,” in July 2009. “But then you realize that it’s really silly,” she said.
Mr. Justin Theroux
Even though the movie’s director and actor, Ben Stiller, introduced Aniston and Theroux when they first met in 2007 on the set of Tropic Thunder, they didn’t start dating until 2010, when they worked together again on the set of Wanderlust.
At the 2011 MTV Movie Awards, the couple made their relationship known to the public. On the Spy Who Dumped Me actor’s birthday in August 2012, the couple got engaged.
They got married three years later, but in February 2018, they announced that they were breaking up, saying that it was a “mutual and loving decision.”