Jennifer Aniston Dating Timeline: How She Ended Up with Justin Theroux
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Jennifer Aniston

Who is Jennifer Aniston dating now? It can be hard to tell, given the actress’ extensive dating timeline. Aniston’s relationship history includes boyfriends, more than one husband, and possibly even one affair, if rumors are to be believed; the only thing missing from her history is children. And given how high-profile some of her relationships have been, there’s a lot here for fans of Aniston and/or the men in her life to go over and scrutinize. And with that, here’s a full Jennifer Aniston dating list, which hit a lot of checkmarks.

1990: Jennifer Aniston had her first celebrity relationship with Charlie Schlatter, with whom she co-starred on a sitcom based on the hit film Ferris Bueller’s Day Off. The two stars played siblings. The show only ran for one season, which is about how short this relationship was.

1995: In ’95, Jennifer Aniston was somewhat briefly dating Adam Duritz, frontman for the band Counting Crows. They went out for most of the year before breaking up, with one notable tidbit later being made public: according to Duritz, he and Jennifer Aniston never slept together. Duritz would go on to date Aniston’s Friends co-star Courteney Cox, though he broke up with her as well. Later that year, Aniston chose to have art imitate life, hooking up with Tate Donovan, who played her character Rachel’s love interest on Friends. They made it quite far, supposedly even getting engaged at one point (the first of several engagements for Aniston).

1998: Aniston and Donovan called it quits early in the year. Speculated reasons for the split included Aniston rushing Donovan to the altar and Donovan having an issue with making less money than her. In the spring of ‘98, not long after breaking up with Tate Donovan, Jennifer Aniston began her most prolific celebrity relationship with Brad Pitt. The two were set up on a blind date by their agents.

2000: Following two years of a harmonious relationship, the two wed in Malibu on July 29, 2000. The super-famous couple, who had their every action heavily observed and scrutinized by the media, enjoyed a wedding with 200 guests (many of whom are also famous), a choir, bands, fireworks, incredibly fancy food, rings designed by her new husband, and over 50,000 flowers.

2005: Despite being expected to butt the trend for celebrity marriages crashing and burning, Jennifer Aniston and Brad Pitt announced they were separating on January 7, 2005, finalizing their divorce much later, on October 2 of the same year. In the period in-between the announcement and divorce, it was suggested that the split was caused by Pitt having an affair with Angelina Jolie, whom Pitt, of course, hooked up with shortly after his split from Aniston. Fans ended up taking sides between Aniston and Jolie and media speculation ran rampant long after the divorce was finalized, even still occasionally being brought up today.

Another possible reason given was that Jennifer Aniston didn’t want children, while Brad Pitt did, which the actress denied, saying she did want kids, but not at the cost of her career.

In late 2005, Aniston rebounded by landing another famous boyfriend, actor Vince Vaughn.

2006: After about a year together, Aniston and Vaughn called it quits. They had tried to give the media the impression that things were fine, including Vaughn suing tabloids that were trying to say he was having an affair, but as they began to spend more time apart, it became clear that this was just another blip on the Jennifer Aniston dating timeline.

2007: Aniston briefly dated actor and model Paul Sculfor. Nothing of note came of it and they parted ways soon after.

2008: This year saw Aniston hook up with singer-songwriter John Mayer at a party. They were only together for a year, but the media made it out to be like Mayer was the second coming of Brad Pitt, as hopes were high that this celebrity couple could make it work for the long haul.

2009: The couple parted ways in 2009 and things did not end well. Mayer took it especially hard, saying their age gap was a big factor in the split, a famously harsh quote of his being, “The brunt of her success came before TMZ and Twitter. I think that she’s still hoping it goes back to 1998.” He also said that he wasn’t happy with how things ended and that it still bothers him to this day. This was also the year that saw rumors about Aniston dating both Bradley Cooper and/or Aaron Eckhart, but if true, they clearly weren’t more than brief flings or maybe even one-night stands.

2011: The newest and current man on the Jennifer Aniston dating list is actor and director Justin Theroux, who began dating the actress in May of 2011. They actually met back in 2007, on the set of Tropic Thunder, becoming official friends in 2010 when they co-starred in Wanderlust. However, this was the year she officially made Theroux her boyfriend.

2012: The pair bought a $22 million home together and, more importantly, got engaged on August 5. Theroux actually took quite a risk with his proposal, popping the question on his birthday.

2015: Jennifer Aniston and Justin Theroux got married on August 5, 2015—exactly three years after the proposal—in the aforementioned $22 million residence. So far so good, but with Jennifer Aniston, can we ever be completely sure?

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