Why Does Jennifer Aniston’s First Marriage Continue to Haunt Her?

Is there anyone in the world who doesn’t think Jennifer Aniston and Brad Pitt looked perfect together? Back in the late 1990s and 2000s, they were the “it” couple. Their blonde locks, sun-kissed skin, and successful careers made them seem like the perfect pair. Maybe they were at some point, but something happened along the way that sent that perfect pairing careening towards divorce. In the sordid mess that followed, fans took sides. They battled it out over who made the better mate for Pitt. They analyzed every forlorn look photographers managed to capture.

Everyone involved in the twisted carnage of their failed marriage managed to make it out unscathed. Pitt went on to have several children with Angelina Jolie. Aniston dated plenty of suitable men. All seems well in their worlds, even if there have been a few bumps in the road. But, still, everyone wonders if the first marriages managed to somehow play a role in the unraveling of their seconds. The answer isn’t cut and dry though. Regardless of their Hollywood star statuses, Aniston and Pitt’s relationship was complicated, just like everyone else’s.

Jennifer Aniston and Brad Pitt are the ‘ship that won’t go away’

In the decade since Jennifer Aniston’s divorce from Brad Pitt tabloids have exclaimed that they have gotten back together, that Aniston is once bitten and twice shy, that Pitt’s marriage to Aniston was a sham all along, and everything in between.

In the years since Aniston announced her separation from her second husband, Justin Theroux and Pitt’s split from alleged temptress, Angelina Jolie, the fodder around the former flames has only picked up steam. Rumors have swirled that George Clooney set the former lovers up in a bid to see Pitt happy. Media outlets have suggested the pair remarried in a secret impromptu ceremony and that they are currently holed up in Pitt’s beachside villa.

Jennifer Aniston and Brad Pitt
Jennifer Aniston and Brad Pitt | Photo by Kevin Winter/Getty Images

Apparently, none of it is right. Aniston and Pitt are simply two formerly married people who have maintained a friendship. The only people holding out hope for a rekindling seems to be the public, and it makes perfect sense. Aniston’s sitcom fame and girl-next-door good looks were perfectly suited to Pitt’s steamy exterior and rocketing movie career. Time marches on for everyone though. The pair seem to have grown apart, and that happened way back in 2005. 

Why did Jennifer Aniston and Justin Theroux split?

According to The Cut, Theroux and Aniston called it quits because of their different lifestyles. Allegedly, Aniston was perfectly content to hang with her close-knit group of Hollywood pals, but the much edgier Theroux preferred the New York art scene. Aniston reportedly had no desire to infiltrate that crowd. 

In August 2018, Aniston sat down with InStyle to discuss her life, upcoming projects and the misconceptions about her love life. Aniston, then 49, spoke briefly about her sudden split from Theroux stating; “It’s pretty crazy. The misconceptions are, ‘Jen can’t keep a man’ and ‘Jen refuses to have a baby because she’s selfish and committed to her career.’ Or that I’m sad and heartbroken. First, with all due respect, I’m not heartbroken. And second, those are reckless assumptions.”

Media coverage, however, had fans believing that Aniston’s first marriage to Brad Pitt had something to do with the breakdown of Aniston’s second marriage. It’s no surprise. Pitt, who went on to commit himself to Angelina Jolie shortly after the divorce was initiated, seemingly plays into the narrative of every single one of Aniston’s failed relationships.

Maybe there were secret rendezvous and whispered phone calls between the pair. Perhaps there wasn’t, but the marriage that ended nearly two decades ago certainly leaves a legacy that has haunted Aniston since that fateful day in 2005 when the public became aware that Hollywood’s sexiest man alive, and Hollywood’s favorite girl next door called it quits.

Will Aniston ever be able to shake the memory of her first marriage?

While Aniston has happily moved on from her life with Pitt, the public doesn’t seem willing to let the dream of the two together go anytime soon. Media coverage has painted Aniston as a jilted woman, whose sadness permeates every relationship she gets herself into.

Jennifer Aniston
Jennifer Aniston | Photo by Steve Granitz/WireImage,

In verified interviews, though, that’s not the Aniston that is projected. In sit-downs with major media outlets, Aniston seems poised, thoughtful, and kind to a fault. She seems carefree, loving, and has just enough of a free spirit to look at divorce and breakups differently than the general public.

She has publicly stated that she doesn’t consider any of her relationships, or her two marriages, failures simply because they ended. Most of mainstream America would consider divorce the ultimate failure, but Aniston seems dedicated to looking at things in a positive light. Will she ever get out from under the memory of her first marriage? Sure she will. Will the American public ever let it go? That’s a different question entirely.