Exploring Jennifer Aniston’s Love Life: From Brad Pitt to Justin Theroux

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Jennifer Aniston expresses gratitude for her past relationships with Brad Pitt and Justin Theroux, stating that they were successful in her personal opinion and ended because they chose to prioritize their own happiness. Despite bumps in the road, Aniston believes that staying in a situation out of fear would do a disservice to her one life. She is now looking for a relationship outside of the entertainment industry, which may be influenced by her parents’ divorce when she was young and her desire to avoid sacrificing her identity in a relationship. Aniston’s dating history includes high-profile relationships, but she has expressed a preference for dating outside of the industry.

Back in 1990, the talented actress Jennifer Aniston took on the role of Jeannie in NBC’s sitcom Ferris Bueller, inspired by the popular movie Ferris Bueller’s Day Off. The series only aired for a total of 13 episodes, during which Aniston met Charlie Schlatter, who played the leading man. Years later, in 2014, Jim Nelson, the Editor-in-Chief of GQ, disclosed his experience as a Hollywood assistant and revealed that the on-screen siblings had a brief off-screen romance, which he personally witnessed while working as a writer’s assistant on Ferris Bueller. Nelson further noted that everyone on set found Aniston attractive, including Schlatter – with whom she had a brief but passionate affair, even though they played brother and sister on the show.

Aniston was in a relationship with actor Daniel McDonald from 1990 to 1995 before he passed away from brain cancer in February 2007, according to Playbill. Aniston spoke affectionately about McDonald in a 2015 interview with The New York Times, calling him her first love and saying that they were together for five years. She also admitted that she made some foolish mistakes when she was younger and that McDonald would have been the one for her. However, she believes that fate intervened when she met Justin Theroux, whom she credits as being sent to her by McDonald as a way of making up for lost time.

Back in 1995, Jennifer Aniston had a brief fling with Adam Duritz, the lead singer of Counting Crows. They met at The Viper Room and hit it off. In an interview in 2021, Duritz revealed that he was unaware of Aniston prior to their encounter. However, mutual friends had lied to each of them and convinced them that the other had a crush on them. Regardless, Duritz found her to be nice, funny, pretty, and someone who liked him back. Though their relationship didn’t last long, he speaks fondly of her as a nice girl.

In 1995, the well-known actress from the movie Picture Perfect began a romantic relationship with Tate Donovan, an actor who had recently ended his affair with Sandra Bullock. Interestingly, Donovan was cast as Rachel Green’s love interest in Friends in 1998, just as his relationship with Aniston came to an end. Aniston made a humorous comment to Bullock in 2020, speculating that Donovan has a certain type of woman that he prefers to date. After splitting with Aniston, Donovan married Corinne Kingsbury a few years later, although they eventually divorced in 2008. There is no doubt that Aniston has had her share of high-profile relationships, including one with Brad Pitt.

Jennifer Aniston and Brad Pitt were introduced to each other by their managers in 1994, but they only went on their first date in 1998. Their relationship flourished as they made their red carpet debut at the 51st Emmy Awards in 1999 and announced their engagement in November of the same year at a Sting concert where they showed off Aniston’s ring. They exchanged vows in front of 200 guests at a private estate in Malibu on July 29, 2000, in an event that included a live performance, 50,000 flowers, and a fireworks show.

Pitt made a guest appearance on Friends in 2001, playing a character who hated Rachel Green. As the show approached its end, Aniston hinted that she and Pitt might be ready to have children. However, rumors began to surface that Pitt had become close friends with Angelina Jolie while filming Mr. & Mrs. Smith. In January 2005, Aniston and Pitt announced that they were separating after five years of marriage, and their divorce was finalized in October of the same year.

Although they remain committed and caring friends, their relationship remains platonic. Vince Vaughn was then seen accompanying Aniston to events.

Back in the summer of 2005, Jennifer Aniston and Vince Vaughn started dating while shooting The Break-Up in Chicago. According to Vaughn, Aniston was an amazing person with a lovely warmth and likability about her. However, by December 2006, their relationship came to an end. Their reps confirmed that they decided to split but remained good friends. Aniston did not speak publicly about the breakup until 2008 when she fondly remembered the time she spent with Vaughn. She referred to him as her “defibrillator” who brought her back to life, and said that he was perfect for the time they spent together. Later on, Aniston dated John Mayer.

Aniston and John Mayer started dating on-and-off around 2008 after meeting at an Oscars party. However, they ended their relationship for good in August of the same year. The singer revealed to reporters that he called it quits to avoid wasting someone’s time if things were not right. The couple briefly reconciled in February 2009 and attended the Oscars together. Still, they decided to part ways again soon after due to disagreements. An insider revealed that the actress is moving on with her life as she always does. In 2010, Mayer admitted that the breakup was one of the worst times of his life.

Back in 2007, Jennifer Aniston and Justin Theroux first met on the set of Tropic Thunder while the former went to meet her friend and former co-star Ben Stiller. Their paths crossed again in 2010 while filming Wanderlust and soon the two started living together by August 2011. They got married on Aug. 5, 2015, in a private wedding ceremony at their Bel Air, California home, tricking their friends and family into thinking that it was Theroux’s 43rd birthday party. The couple announced their separation in February 2018, after two-and-a-half years of marriage. In a statement, they mentioned that it was a mutual decision and they had parted ways as a couple but would continue being good friends. Despite the split, Aniston and Theroux have maintained their friendship and have supported each other through the years, celebrating each other’s birthdays and staying in touch.