Jennifer Aniston’s friendship with Chelsea Handler suffered after an ‘innocent’ mistake turned bothersome

LOS ANGELES, CALIFORNIA: Jennifer Aniston’s friendship with Chelsea Handler suffered a major blow after what started as an “innocent” mistake on the 50-year-old comedian’s part took a bothersome toll. 

As reported by the Daily Mail, the 56-year-old ‘The Morning Show’ star and Handler’s friendship spans more than a decade, and the duo once appeared inseparable. Friendship blossomed between the two women in 2009 when Aniston appeared on Handler’s late-night talk show ‘Chelsea Lately’ as a guest. 

There was a time when Aniston and Handler were close — from award shows to vacationing, the besties looked inseparable. In fact, a source spilled that Handler would also lend an ear to the ‘Murder Mystery’ actress when she was angst-filled regarding her love life. 

However, the insider shared that the fervor of their friendship cooled down after the ‘Friends’ alum thought the ‘Chelsea Does’ star was spilling too much to the media.

Real reason behind cooling down of Jennifer Aniston-Chelsea Handler friendship

Though Jennifer Aniston and Chelsea Handler were seen posing together at the Critics Choice Awards in January last year, the source shared that their friendship has suffered a blow after the ‘Fun Size’ star started revealing more about her friend’s life in interviews. 

“Jen wants to be more private, while Chelsea wants to be front and center, so perhaps a breakdown was always inevitable,” shared a source close to Aniston, and reflected, “They jumped into their friendship headfirst and went from not knowing each other to being together 24/7.”

Nevertheless, the source clarified that despite their friendship, Handler thought that they were much closer than they were. 

Initially, their friendship was solely based on their shared humor, but gradually, the two friends started conversing about Aniston’s tumultuous love life as well. Amid this, Handler started publicly calling out Angelina Jolie, for her alleged role in Aniston’s divorce from Brad Pitt. 

The ‘We’re the Millers’ actress was married to the ‘Troy’ star for years when Pitt went on to co-star in the 2005 movie ‘Mr and Mrs Smith’. His marriage with Aniston crumbled as Pitt fell in love with Jolie, ultimately leading to a divorce in 2005. 

Pitt and Jolie eventually dated for another decade before tying the knot in 2014. Nevertheless, their association ultimately came to an end when Jolie filed for a divorce in 2016. 

However, in 2014, Handler started publicly criticizing Jolie and called her “a f***ing lunatic.”

Speaking in an interview, Handler said, as reported by the outlet, “There are rumors that part of the problem was that Brad was allegedly drinking and smoking too much weed. I wonder why he would need to self-medicate.”

“Maybe because he could have been spending the last 12 years at Lake Como hanging out with George Clooney and Matt Damon, instead of being stuck in a house with 85 kids speaking 15 different languages,” continued Handler, and added, “Oh yeah, because he married a f***ing lunatic, that's why.”

In 2016, she again threw shade at Pitt and the ‘Maria’ actress, and said in an interview with Grazia that “it's so stupid and pathetic” that everyone thinks Aniston was still fixated with her ex’s love life. 

However, her aggressive defending of Aniston in interviews reportedly had the opposite effect. Her fiery speech dragged Aniston into a drama of which she no longer wished to be a part. 

The insider shared that while it began as something “innocent,” it slowly started to bother Aniston. After a while, she allegedly even felt that Handler was bringing up Jolie for the sake of publicity.

Chelsea Handler and Jennifer Aniston’s friendship suffered during her marriage to Justin Theroux

Not only Chelsea Handler’s comments on Angelina Jolie, but also her certain comments about Jennifer Aniston’s second marriage to Justin Theroux reportedly widened the chasm. 

Another source shared that at that time, Theroux thought Handler to be “rude and obnoxious” and that she encouraged Aniston “to act like she's single".

When Aniston’s marriage with Theroux was breaking down in 2017, the actress was reportedly left paranoid that her private life would once again be the center of attention. 

“Jennifer became paranoid, thinking that people around her were leaking stories to the press,” said the source, before adding, “Chelsea was still talking about Jennifer in interviews, and Jennifer automatically pointed the finger at her.”

A source even said that after years of friendship, Aniston and Handler’s connection has reportedly suffered a blow and that it is “not the same as it was, and it will never be.” They also hinted at “jealousy” to be a reason, as the source noted, “Chelsea seemed willing to do anything to be a star, and Jennifer was already a big name so of course there were hints of jealousy.”

Another insider noted that Aniston has “a wide group of friends which at one time included Chelsea, but she never made it into her inner circle like Courteney Cox or Jimmy Kimmel.”

While the duo still maintains a cordial relationship, the sources reveal that the chances of them having a “serious friendship” again are low.