Jennifer Aniston's Most Painful Relationship Confessions

She rose to prominence playing Rachel Green in one of the most-loved American sitcoms of all time and then went on to prove herself as a movie star, but Jennifer Aniston has unfairly become better-known for her failed relationships than her career achievements. Friends made her a fashion icon and America's biggest sweetheart, but her influence hit another level when she began dating A-list heartthrob Brad Pitt. The two married in a lavish Malibu ceremony in 2000, cementing their status as Hollywood's hottest new power couple.

As we all know, Aniston wound up handing her crown over to Oscar-winning actress Angelina Jolie, who took her man and usurped her as the unofficial queen of Tinseltown. Brangelina became everyone's new favorite word, and Aniston was left to lick her wounds, choosing to do so primarily in private. Aniston makes no secret of her distrust of the press, but the actress has occasionally opened up about her complicated love life.

In February 2018, she split from her second husband, actor Justin Theroux. They vowed to go about their separation in a respectful manner, but things are never quite that simple in Hollywood. Just like she did the first time around, Aniston has carefully begun to reveal her relationship woes, and some of it makes for pretty unpleasant reading. From cheating rumors to fabricated baby dramas, here are Jennifer Aniston's most painful confessions.

During an illuminating interview with Vanity Fair in 2005, a newly separated Aniston made a shocking claim about her equally shocking split from actor Brad Pitt: She had no idea that Pitt might have cheated on her with his soon-to-be-girlfriend, Angelina Jolie. Instead, Aniston claims that when she and Pitt released their joint statement about why they were parting ways, what was "said was true as far as [she] knew."

"We wrote it together, very consciously, and felt very good about it. We exited this relationship as beautifully as we entered it," she said.

Except the exit wasn't exactly beautiful. Not long after the divorce was announced, Pitt and Jolie were photographed frolicking together on exotic beaches. The sight was somewhat of a slap in the face to Aniston, who'd gone out of her way to defend her ex when he was accused of being unfaithful. Sources close to Aniston at the time told Vanity Fair that while she wasn't naive about Pitt and Jolie's closeness, she didn't think there was anything more than a deep friendship or emotional attachment.

"The world was shocked, and I was shocked," Aniston said. "I can't say [seeing Brad with Angelina] was one of the highlights of my year. Who would deal with that and say, 'Isn't that sweet! That looks like fun!'?"

The public's obsession with the Aniston-Pitt divorce wasn't solely about whether or not Brad Pitt cheated on Jennifer Aniston with Angelina Jolie. There was also a hurtful, outright sexist accusation made against Aniston at that time: that the primary reason Pitt left Aniston was because he wanted a family. Meanwhile, Aniston supposedly wanted to focus on her career and put off pregnancy as long as possible. The cruel claim made Aniston seethe. "A man divorcing would never be accused of choosing career over children," she told Vanity Fair in 2005, admitting that the baseless gossip "pissed [her] off." 

"I've never in my life said I didn't want to have children," she said at the time. "...The women that inspire me are the ones who have careers and children; why would I want to limit myself?"

Jennifer Aniston finally took aim at the press in a powerful essay for The Huffington Post in 2016. In the no-holds-barred piece, she called out the public's ludicrous obsession with her relationship status and whether or not she'd ever be a mom. 

"The objectification and scrutiny we put women through is absurd and disturbing. The way I am portrayed by the media is simply a reflection of how we see and portray women in general, measured against some warped standard of beauty..."she wrote. "...The sheer amount of resources being spent right now by press trying to simply uncover whether or not I am pregnant [points] to the perpetuation of this notion that women are somehow incomplete, unsuccessful, or unhappy if they're not married with children."

Aniston was clearly over it, and wanted to make it completely clear that who she is as a woman and actor is far more than the narrow scope through which women are viewed in a highly misogynistic society. "Yes, I may become a mother some day," she said, "...But I'm not in pursuit of motherhood because I feel incomplete in some way, as our celebrity news culture would lead us all to believe."

She'll forever be associated with Brad Pitt, but Jennifer Aniston has been romantically linked to a number of other Hollywood stars over the years. Paul Rudd, Vince Vaughn, Orlando Bloom, Owen Wilson, Gerard Butler and Aaron Eckhart are all rumored to have dated the former Friends star, though Aniston has made separating fact from fiction rather difficult by keeping her personal business as far from the press as possible. But one thing's for sure — she knows a thing or two about a breakup.

When it comes to coping with a relationship gone wrong, Aniston admits that "there are stages of grief" that one must go through to heal. "It's sad, something coming to an end. It cracks you open, in a way — cracks you open to feeling," she told Vanity Fair in 2005. "When you try to avoid the pain, it creates greater pain. I'm a human being, having a human experience in front of the world. I wish it weren't in front of the world. I try really hard to rise above it."

Try as she might, the actress admitted that she would still throw the odd "pity party" after she and Pitt split. She insisted she was proud of how well she'd managed to cope, yet the actress was clearly in a dark place while speaking with Vanity Fair after her very public divorce. "Am I lonely? Yes. Am I upset? Yes. Am I confused? Yes."

Perhaps the most heartbreaking line in Aniston's lengthy and candid interview with Vanity Fair is the one in which she compares herself to the most vulnerable Disney character ever. "It's sort of like Bambi — like you're trying to learn how to walk," she said. "You're a little awkward; you stumble a little bit." 

The actress had plenty of reasons to be mad at Brad Pitt. Among them: He decided to pose alongside Angelina Jolie as a married couple in a 60-page spread for W magazine not long after the split! Aniston said the spread proved Pitt was missing a "sensitivity chip," but even so, she opted to take the high road.

It's easy to criticize an ex when things go south, but the Horrible Bosses star learned from her long-time therapist to accept her own role in failed relationships. "To live in a victim place is pointing a finger at someone else, as if you have no control," Aniston said. "Relationships are two people; everyone is accountable."

Sadly, Aniston's therapist passed away in the middle of her divorce from Pitt. "It was a crazy time," she told The Hollywood Reporter. "I learned so much in the four years I worked with her, that when she did pass away I remember thinking, 'Wow, everything that we talked about and discussed, it's allowed me to be really peaceful about it all.'" Aniston still meditates on a regular basis.

Both parties have to be on the same page for a relationship to function, and this just wasn't the case with Jennifer Aniston and Brad Pitt. Following their high-profile break-up, Aniston revealed that they simply "believe in different things" when it comes to maintaining a healthy marriage. "You can't force a relationship, even if it's your view of how you would like it to be conducted," the actress told Vanity Fair. "Obviously two people leave a relationship because there's a different thought pattern happening."

The actress said her goal going forward was to "try and achieve a very deep, committed relationship." She seemed to have found that with Justin Theroux. The two met on the set of the 2012 comedy Wanderlust and married in a secret L.A. ceremony in August 2015, according to the BBC. In February 2018, they released a joint divorce statement saying they were looking forward to continuing their "cherished friendship." What happened this time?

We can't say for sure, but according to People, sources claimed Theroux didn't want to give up New York for Los Angeles, and Aniston found life "miserable" in NYC. "They couldn't find common ground that made them both happy. It became exhausting and frustrating." The insider said Aniston was "sad and disappointed" because she "didn't expect to be single again."

In August 2018, Aniston gave one of her most revealing interviews in a long time, sitting down with InStyle to discuss her life post-Justin Theroux. Interviewer and friend Molly McNearney broached the topic of the Time's Up movement during her sit-down with Jen (as she calls her), and Jen revealed that she'd had her share of unwanted attention over the years.

"I've definitely had some sloppy moves made on me by other actors, and I handled it by walking away," a 49-year-old Aniston said. Interestingly, most of the unpleasant encounters she's been caught up in actually involved members of her own sex. "In my personal experience, I've been treated worse verbally and energetically by some women in this industry," she said. 

However, Aniston's personal experience doesn't tally with a staggering number of women working in film and TV, and she is well aware of this fact. In January 2018, Aniston and a host of other A-listers, including Reese Witherspoon and Meryl Streep, donated a whopping $500,000 each towards the Time's Up legal defense fund. Aniston believes the Time's Up movement can lead to real change for women in Hollywood. "It's long overdue," she told InStyle. "But we also need to be better at listening to one another. That includes men. They need to be part of this conversation. When everyone is mad and aggressive, people become too afraid to speak and there is no conversation."

Jennifer Aniston's relationship with the press has always been a complicated one. In recent years, she's gone out of her way to call out certain sectors of the media for what she deems to be an unhealthy obsession with her personal life. She and Justin Theroux even took a shot at the "gossip industry" in their joint divorce statement, getting in ahead of the celeb mags before they got the chance to "speculate and invent." When she spoke to InStyle, Aniston argued that she wouldn't be reported on in the same way if she were a man.

"I've definitely had my fair share of sexism in the media," she said. "Women are picked apart and pitted against one another based on looks and clothing and superficial stuff. When a couple breaks up in Hollywood, it's the woman who is scorned. The woman is left sad and alone. She's the failure. F that. When was the last time you read about a divorced, childless man referred to as a spinster?"

To her annoyance, the rumors that plagued her when she and Brad Pitt divorced were recycled after she and Theroux called it quits. "It's pretty crazy," she said. "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.'" 

Aniston's publicist even had to come out and deny reports she was using Pitt as a shoulder to cry on, calling the story "a complete fabrication."

True to form, Aniston didn't go into much detail about her separation from Theroux when she spoke to InStyle, but what she did say, spoke volumes and generated headlines everywhere. "First, with all due respect, I'm not heartbroken," she told InStyle. "And second, those are reckless assumptions. No one knows what's going on behind closed doors."

Though Aniston may have simply been pushing back against sexist breakup narratives, others claimed she was taking a subtle shot at her ex. An insider told Life & Style (via New Idea) that Aniston's interview was a "big 'F you' to Justin" because she "thought this would be an amicable split, but she was wrong." 

According to Radar Online, Theroux was blindsided by his ex's comments. "Justin had no heads-up and no idea that Jennifer was doing the interview," a source claimed. "He was heartbroken by her decision. The two of them do not talk anymore and he thought they had both agreed to not talk about each other or their failed marriage in the press." 

Reports like these obviously need to be taken with a pinch of salt, but if the rumors are true, Aniston may be ready and willing to confess a bit more in the future.