Jennifer Aniston Dated a Lot of Lucky Men — See Her Relationship History!

Charlie Schlatter

The California native dated her Ferris Bueller Show costar Charlie Schlatter for a short time in 1990.

Daniel McDonald

Ah, who could forget their first love? In an interview with The New York Times, Jen talked about Daniel McDonald, whom she dated for several years. Unfortunately, the Tony nominee passed away in 2007 from a brain tumor. “He was my first love — five years we were together. He would have been the one. But I was 25, and I was stupid,” she said. “He must have sent me Justin [Theroux] to make up for it all.”

Adam Duritz

Not her typical type! The Golden Globe winner dated Adam Duritz, the lead singer of the Counting Crows, in 1995.

Tate Donovan

Jen’s first fiancé was Tate Donovan. They started dating in 1995 after they were set up by mutual friends. As their relationship was ending, Tate appeared on an episode of Friends, and let’s just say it was awkward for both of them.

Brad Pitt

Golden couple! The pair started dating in 1998, got married in 2000 and split in 2005 after Brad Pitt admitted he had fallen in love with Angelina Jolie on the set of their movie, Mr and Mrs. Smith. Even though Jen was married to the Fight Club actor a long time ago, it didn’t stop him from showing up to Jen’s birthday bash in February 2020. Brad and Jen also reunited in September of that year for a table read of the 1982 film, Fast Times at Ridgemont High.

Paul Rudd

There were rumors that the two were an item while they filmed The Object of My Affection in 1998. However, Paul and Jen have stayed good friends since.

Vince Vaughn

After working together on The Break-Up, the duo became an item, but tried really hard to keep their romance out of the spotlight. They split after a year of dating in 2006.

Paul Sculfor

Jen was spotted getting cozy with the British model for a couple of months in 2007.

John Mayer

Jen met the musician in February 2008 at an Oscars party. The pair called it quits in 2009 after splitting twice. “I’ve never really gotten over [the breakup],” he told Rolling Stone magazine in 2010. “It was one of the worst times of my life.”

Gerard Butler

The Bounty Hunter costars denied that they were dating in 2009-2010, but they always seemed like there were sparks flying between them.

Justin Theroux

The actress met Justin Theroux while they were filming Wanderlust in 2011. They got married on August 5, 2015, but unfortunately called it quits on February 15, 2018. In an interview with Elle magazine later that year, the brunette beauty revealed that she is doing just fine without a man. “I don’t feel a void,” she said. “I really don’t. My marriages, they’ve been very successful, in [my] opinion.” We love your attitude, girl!

Mystery man

In February 2021, In Touch exclusively revealed that the Good Girl star had  a new mystery boyfriend. “He’s down to earth, handsome, he makes her laugh and he makes her feel safe. She trusts him,” the insider dished at the time.

According to the source, “one of the best things” about Jennifer’s new BF is that “he was never a fan of hers or Friends, which she found so refreshing.” The Los Angeles native played Rachel Green on the hit NBC sitcom from 1994 to 2004.

However, in June 2021, she revealed to People that she is seemingly single and doesn’t like to use dating apps.

David Schwimmer

During the HBO Friends reunion special that aired in May 2021, Jennifer’s costar, David Schwimmer, admitted that he had a crush on her.  “The first season, I had a major crush on Jen,” David said.
Jennifer chimed in and said that the crush was “reciprocated,” but the costars revealed that nothing ever actually happened between them off-screen.
“I remember saying one time to David, ‘It’s gonna be such a bummer if the first time you and I actually kiss is going to be on national television,’” Jen said at the time. “Sure enough, the first time we kissed was in that coffee shop. We just channeled all of our adoration and love for each other into Ross and Rachel.”