Jennifer Aniston’s romantic relationships have been a subject of public interest for many years. Her high-profile marriage to Brad Pitt, which ended in 2005, was a particular source of media scrutiny. Aniston spoke candidly about the pain of their separation and how the rumors surrounding Pitt’s subsequent relationship with Angelina Jolie affected her.

She later found love again with actor and writer Justin Theroux, and although the couple’s intimate wedding was a surprise to their guests, they revealed that they had felt “already married” for some time.

However, after two years of separation, they announced their decision to end their romantic relationship.

Despite the end of their marriage, Aniston and Theroux remain close friends, and they continue to make each other laugh and bring each other joy. Aniston remains optimistic about her romantic life and has emphasized the importance of choosing happiness, even if it means ending a relationship.

Charlie Schlatter

Charlie Schlatter

After collaborating on the short-lived 1990 TV remake of the John Hughes film Ferris Bueller’s Day Off, Aniston and Schlatter generated relationship rumors.

Daniel McDonald

daniel mcdonald jennifer aniston

During an interview with The New York Times in January 2015, the Dumplin’ actress referred to McDonald as her “first love,” “He was going to be The One. But I was just 25 and foolish.”

Before calling it quits, Aniston and McDonald, who passed away in 2007 from brain cancer, dated for five years.

Jon Stewart

Jon Stewart Jennifer Aniston

Over 20 years ago, the comedian and the actress went on one date. In August 2010, Stewart reminded Aniston on The Daily Show, “I asked you out and it was nice. “I recall you having so many of your friends around you. She’s so excited to go out with me, I recall thinking, and she wants me to meet her gang.

The star of The Office Christmas Party disagreed, saying, “If I recall correctly, wasn’t it kind of like, ‘Hey, a number of us are going out, do you want to join?'”

Adam Duritz

Adam Duritz and Jennifer Aniston

In 1995, Aniston and the frontman of Counting Crows had a brief romance. After their breakup, Duritz momentarily moved on with Courteney Cox, who was Aniston’s Friends co-star and best friend in real life. For her part, the Scream star has been dating Johnny McDaid since 2013.

Tate Donovan

Tate Donovan

In 1998, Donovan was happy to be offered a six-episode arc on Friends, but the role was difficult because he and Aniston were going through a divorce at the same time.

“I was simply pleased to join the team. The only disappointment was that Jennifer and I were at the time parting ways, the Argo actor told Us in September 2018.

It was difficult to pretend that we were simply getting to know each other and falling in love or otherwise becoming interested in one another while actually planning to break up. That was really difficult.

Paul Rudd

Paul Rudd and Jennifer Aniston

The Subject of My Love For many years, co-stars kept their alleged romance a secret, but Aniston eventually acknowledged that they were “together when we were, like, 12.”

Also, the actors co-starred in The Newton Boys in 1998, Wanderlust in 2012, and Friends from 2002 to 2004.

Brad Pitt

Brad Pitt and Jennifer Aniston

In 1998, Aniston and the Oscar winner began dating. They later got married in 2000. But the stars surprised the world when they called it quits in 2005 after persistent accusations that Pitt had an extramarital affair with his Mr. & Mrs. Smith co-star, who he had started dating soon after their breakup with the Mother’s Day actress.

After two years of marriage, Pitt and Jolie, who had six children together, divorced in 2016. In 2019, their divorce was finalized.

Vince Vaughn

Vince Vaughn and Jennifer Aniston

The Cake actress moved on from Pitt with Vaughn from Wedding Crashers, but the rumors surrounding the union led to its breakup in December 2006.

The True Detective star told Playboy magazine in February 2015, “You know, she’s fantastic. “Spending time with someone you like and like is separate from liking them; everything was fine. Yet, I actually spent most of that time figuring out how to avoid attracting attention.”

He was great for the time we spent together, and Aniston could not look back on the romance with fondness, stating to Vogue shortly after the separation, “He was lovely and fun.” I also required that. And it sort of completed its journey.

Paul Sculfor

Paul Sculfor and Jennifer Aniston

In 2007, the British model courted Aniston for a short while, but things never got serious. An insider at the time told Us that there was no drama. They “hang out and had a few dinners.”

John Mayer

John Mayer and Jennifer Aniston

From April 2008 to March 2009, the singer and actress had an on-again, off-again relationship.

The “Gravity” singer said on CBS Sunday Morning that he was “just a jerk” while they were dating after their final breakup.

In a later interview with Playboy, he said: “That pearl of possibility that dwells in your heart when you meet someone you want to learn more about has such a different molecular density from everything else that you have to chase it.

I wouldn’t undo it either, guy. I would have benefited if it had worked out, after all. When I get home, I have what I’ve always desired, I would be saying while I sit here.

Bradley Cooper

Bradley Cooper

After appearing together in He’s Just Not That Into You, Cooper and Aniston engaged in a brief romance that summer. They never had a long-term love connection, but they were always cordial.

Gerard Butler

Gerard Butler

Following their roles as co-stars in The Bounty Hunter, Butler, and Aniston became the subject of dating rumors. The Friends alum and the star from Olympus Have Fallen later admitted to Us that they had laughed off dating rumors. He remarked, “It’s a touch silly,” in July 2009. “But then you realize that it’s really foolish,” she said.

Justin Theroux

Justin Theroux Jennifer Aniston

While Ben Stiller, the movie’s director, and actor, introduced Aniston and Theroux when they first met in 2007 on the set of Tropic Thunder, their relationship didn’t begin until they reconnected in 2010 while filming Wanderlust.

At the 2011 MTV Movie Awards, the couple made their relationship public. On the Spy Who Dumped Me star’s birthday in August 2012, the couple got engaged.

They got married three years later, but in February 2018, they announced their split, saying that it was a “mutual and loving decision.”


Jennifer Aniston is an American actress who has had several high-profile romantic relationships. She was married to Brad Pitt from 2000 to 2005, but their relationship ended amidst rumors of an affair between Pitt and his co-star in Mr. & Mrs. Smith, Angelina Jolie.

Aniston subsequently dated and was engaged to actor and writer Justin Theroux from 2011 to 2018. Prior to these relationships, Aniston was in a long-term relationship with actor Daniel McDonald, who she has described as her “first love.”

Aniston has also been romantically linked to several other notable figures in the entertainment industry, including Charlie Schlatter, Tate Donovan, Paul Rudd, Vince Vaughn, John Mayer, Bradley Cooper, and Gerard Butler.

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