Jennifer Aniston’s Dating History: A Complete Timeline of Her Exes and Flings.


Good fortune in life and love! Jennifer Aniston’s dating life has long been a matter of discussion, from her marriage to Brad Pitt through her second marriage to Justin Theroux.

Aniston and Pitt began dating in 1998 and married two years later. Fans were heartbroken when the couple announced their divorce in 2005, after five years of marriage. When it came to their split, the Friends alum acknowledged that there were “many phases of mourning.”

“It’s heartbreaking to see anything come to an end.” In a way, it splits you open—cracks you open to sensation,” she told Vanity Fair in September 2005. When you try to ignore the pain, you make it worse. I’m a human person going through a human experience in front of the rest of the world. I wish that wasn’t in front of the entire globe. I make every effort to climb beyond it.”

Pitt began seeing his Mr. and Mrs. Smith co-star Angelina Jolie shortly after the couple split up. The couple met while the Once Upon a Time in Hollywood star was still married to Aniston, which raised eyebrows.

Daniel McDonald and Jennifer Aniston

Contrary to common perception, Aniston’s first love was actor Daniel McDonald (sorry to break it to you Pitt and Aniston fans).

Before Anistons big breakthrough on Friends, the pair dated for four years, from 1990 to 1994. McDonald died in 2007 as a result of a brain tumour.

In a prior interview, Jennifer stated, “He would have been the one, but I was 25 and foolish.”

Adam Duritz and Jennifer Aniston

Aniston briefly dated Counting Crows member Adam Duritz in 1995 while attempting to move on from her first love, but the relationship ended shortly. Duritz’s claim is that the couple never slept together.

Despite the unusual coupling, we can see why Aniston, an Aquarius, would be drawn to the dynamic Leo, Duritz. It would have been a perfect zodiac match.

Tate Donovan and Jennifer Aniston

Aniston’s first serious boyfriend was Tate Donovan. They dated from 1995 to 1998, and were even engaged briefly at the end. Donovan went above and above as a lover when he surprised Aniston with a dog called Enzo on Valentine’s Day. *squeezes heart*

Their split, on the other hand, was terrible. Despite their recent divorce, Donovan starred on Friends and dated Aniston’s character Rachel.

Paul Rudd and Jennifer Aniston

Jennifer Aniston and Paul Rudd

Aniston and Rudd began dating in 1998, after meeting on the set of The Object of My Affection. In addition, Rudd appeared on Friends as Mike, Phoebe’s future husband. Rudd has encountered Aniston (accidentally) several times during their brief romance and has spilled the beans on his unpleasant encounters with his ex-girlfriend.

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