Jennifer Aniston Has Gone Through Two Major and Public Divorces During Her Quest for Love

Actress Jennifer Aniston is known best for her role as spunky Rachel Green on Friends. Just like her character, Jennifer is upbeat and has a complicated dating history.

The star's life has had a microscope on it since the early days, so fans have watched her fall in and out of love many times in her life. Some breaks were harder than others.

Jennifer's first big celebrity relationship came after her performance on Ferris Bueller where she met Charlie Schlatter. However, it wasn't a super public one. The world only really found out years later when GQ's Editor-in-Chief Jim Nelson reported on it.

"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. Jim had the inside scoop from when he worked behind the scenes in the world of entertainment.

Jennifer moved on to Daniel McDonald who she dated for five years. In 2007, he died from brain cancer. The actress previous said that he was her first love. She told The New York Times: "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 Durtiz of the Counting Crows sort of got punked into dating Jennifer and vice versa. Apparently, their friends set them up back in 1995 ahead of their brief relationship. His friends told him Jennifer had a crush on him and hers said the reverse to her.

"I honestly had no idea who she was," he told PEOPLE. Regardless, they ended up going along with the prank and got together. Adam had nothing but nice things to say about her and the short relationship, but some things just don't work out.

Tate Donovan's fallout with Sandra Bullock led him to the arms of Jennifer. In 1995, she was in the middle of filming the legacy television show Friends. Tate was cast as Rachel Green's love interest after meeting, they started crushing on each other off-screen, too.

Here comes the drama! Jennifer and Brad Pitt's relationship is marked down in entertainment history as it was plastered all over tabloids. They started dating in 1998, making their red carpet debut at the 51st Emmy Awards only a year later. They were quick to get engaged, making it official by the end of that year.

After they were married, Brad even had a little cameo on Jennifer's Friends. Afterward, everything started getting even more serious as Jennifer started to consider settling down and starting a family.

That is until... Brangelina. Rumors started swelling about some chemistry between Brad and Angelina Jolie. In a suspicious timing, Brad and Jennifer announced that they were done, but told PEOPLE that the "separation is not the result of any of the speculation reported by the tabloid media."

Of course, Brad and Angelina went on to have a very chaotic, heavily publicized relationship. That being said, that hasn't been much public tension between all of them since it was all settled.

Everything seemed to be going great until... Brangelina. As rumors started heating up that something was happening between Brad and Angelina Jolie, Jennifer and Brad announced they were splitting up. However, they claimed to PEOPLE that their "separation is not the result of any of the speculation reported by the tabloid media."

Jennifer dated Vince Vaughn briefly, starting in summer 2005. However, they ended up splitting by 2006. In retrospect, Jennifer admitted that the relationship was right for the moment, but just wasn't meant to be forever. She said he really helped her love life a bit more again.

A muddy situationship formed between singer John Mayer and Jennifer Aniston in 2008. The relationship was never quite stable and it didn't seem like a big deal at the time, but a few years later Jennifer vaguely confessed: "I've never really gotten over it. It was one of the worst times of my life."

Justin Theroux is Jennifer's second ex-husband. She met him through Ben Stiller and their relationship progressed relatively quickly. In August 2011 the moved in together, setting themselves up for a serious relationship.

In 2015 they had a surprise wedding. They told their friends and family that the event was just a birthday party, but once they were there they started with the nuptials. Unfortunately, they went their separate ways in 2018.

"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."