Jennifer Aniston has never been an ordinary human being, as she is an industry unto herself as an actress, and if fans want to know about her personal life, she is a library to describe everything about her love, relationships, heartbreak, and more.

Aniston’s hit comedy Friends, which graced home screens in 1994, catapulted her into the spotlight. From her impact on fashion and style on generations of women to her millions of followers on Instagram, she has been an influential force for more than two decades. The 53-year-old actress has won numerous acting awards and her love life has also wowed fans. Many of Aniston’s past relationships have been with other celebrities, creating an even greater spotlight on the men in her life.

The animator’s first romantic story, which reached the tabloids, was with fellow actor Tate Donovan. The Upside star admitted to InStyle magazine that he never watched Friends and that he didn’t know her. After three years of dating, the couple got engaged in 1998 but split soon after.
After the breakup, Donovan joined the cast of Friends as Rachel Green’s love interest Joshua Burgin. The split caused conflict on set and resulted in Donovan’s character only lasting six episodes.

He also had a brief romance with his Friends co-star and romantic partner on the series, as everyone’s favorite Friends couple Jennifer Aniston and David Schwimmer almost became a real-life couple as well.

Following her romance with the OC alum, Aniston began dating Brad Pitt after they were set up by their respective agents. Billed as a power couple, they were considered one of the most successful marriages in Hollywood at the time.

The celebrity duo split in 2005 after five years together as a married couple, which sparked some controversy when Brad quickly moved on with his Mr. and Mrs. Smith co-star Angelina Jolie.
Justin Theroux, meanwhile, is his most recent serious romance. The two met on the set of Tropic Thunder in 2007 but didn’t start dating until years later, after starring together in 2019’s Wanderlust. Theroux and Aniston married in 2015 but announced the end of their relationship two years later.

Even after the split, the couple remains close friends and have met on many occasions. The Leftovers alum posted a thoughtful Instagram in 2019 for the Cake star’s 50th birthday, writing, “Happy birthday to this fierce woman. Fiercely caring. Fiercely kind…and fiercely funny. You B.”

The Friends star has been candid about her love life over the years. The actress weighed in on ex Daniel McDonald, who sadly passed away in 2007, in a 2015 interview with The New York Times, noting that he could have been “The One” if she were older and wiser. “He was my first love: five years we were together. He would have been the one,” the Emmy winner said at the time. “But I was 25 and stupid. He must have sent Justin to make up for everything.”

Although they enjoyed much of their time in the Hollywood spotlight, Aniston and Pitt did a couple of average things like everyone else. “It’s like the ebb and flow of every relationship,” he told Vanity Fair in 2005.

Aniston once fielded questions about her, Pitt, and Jolie’s infamous love triangle.
“[My therapist’s] main focus is that one day you’re a victim, and that’s it. So we take responsibility for our input. Relationships are two people; everyone is responsible. It takes a lot for a relationship to come together, and a lot for a relationship to fall apart,” the Marley and Me star shared with Vanity Fair.

Jennifer Aniston’s mindset paid off. Since her time on the hit show, she has starred in several notable projects, including her acclaimed role in the film Cake and her recent award-nominated performance on The Morning Show.

Aniston fans still believe she has the potential to spark beautiful new beginnings, even if we can’t see it at the time.