Everyone Jennifer Aniston Has Dated, From Brad Pitt to Justin Theroux

Aniston was linked to the Counting Crows frontman for a short time in 1995 — however, according to Us Weekly, he's said in interviews that they "never even slept together." In 1997, Duritz went on to date her "Friends" costar (and real-life BFF) Courteney Cox.

The couple began dating in 1995 and had already been together for a while before he played her love interest Joshua on "Friends." However, Donovan said "didn't know who" Aniston was before dating her and had "never seen 'Friends,'" per E! News. There were rumors that Aniston and Donovan got engaged in 1997, but Aniston told People (via E! News), "There's nothing to report. You have to take more time to get to know someone." They eventually broke up in 1998.

Rudd played Aniston's gay best friend in the 1998 rom-com "The Object of My Affection," and the two were rumored to have struck up a brief romance, per Page Six. The two stayed friends and even worked together a few more times; Rudd starred as Lisa Kudrow's onscreen husband, Mike, on "Friends," and he and Aniston starred as a couple in 2012's "Wanderlust." (Fun fact: Aniston fell in love with Justin Theroux on the film's set in 2010.)

While promoting the film, the duo were asked in an interview with GQ if it was "weird to kiss" on screen, having been close for such a long time. Aniston remarked, "Nah. I've kissed him for years," while Rudd quipped, "We've made out for decades."

We'll keep things short so as not to make anyone sad: Pitt and Aniston were Hollywood's golden couple from 1998 to 2005. They split after Pitt fell in love with Angelina Jolie on the set of "Mr. and Mrs. Smith." Despite their split, however, Pitt and Aniston appear to be on good terms now.

After her split from Pitt, Aniston began dating her "The Break-Up" costar, Vince Vaughn. The two were together for a year before going their separate ways in December 2006. Of dating Aniston, Vaughn told Playboy (via E! News), "You know, she's great. For me personally — and I think most well-known actors who are together feel this way — I never enjoyed the paparazzi side of it."

Aniston was rumored to have romanced the very handsome (and very British) model Paul Sculfor for a couple of months in 2007, per People.

In 2008, Aniston began seeing singer John Mayer, who by then had become widely recognized as a Hollywood womanizer. Despite the headlines, the two dated for 11 months and seemed to be very much in love; Mayer confirmed as much in an interview with Playboy after their breakup, saying, "I wouldn't undo it, man. Because if it had worked out, I would have reaped the benefits. I would be sitting here saying, 'What I have when I go home is the thing I've always wanted.'"

Mayer also alluded to still having feelings for the actor after their split. "We just have a regard for each other's feelings that is pretty intense. It's been a deep relationship, and it's no longer taking place at all. Have you ever loved somebody, loved her completely, but had to end the relationship for life reasons?"

Aniston seemed to have found her forever with actor Justin Theroux, who she counted as a friend for years but reconnected with on the set of "Wanderlust" in 2010. They tied the knot in a surprise ceremony in August 2015 and shared lots of sweet moments together on the red carpet, but, sadly, their relationship came to an end in 2017. Aniston's rep released a statement to POPSUGAR in February 2018, saying the "decision was mutual and lovingly made at the end of last year." The former couple also added that "they look forward to continuing our cherished friendship."

In 2021, Theroux told Esquire that he and Aniston have stayed true to that intention. "I would say we've remained friends," he said, adding that he and Aniston still "love each other" even though their relationship has ended. "I'm sincere when I say that I cherish our friendship," he continued. "We can not be together and still bring each other joy and friendship."