As the 20th anniversary of Jennifer Aniston and Brad Pitt's breakup approaches, the actress is looking back at the dramatic period when her ex-husband was romantically linked to his Mr. & Mrs. Smith co-star, Angelina Jolie.

The breakup, which made headlines worldwide, sparked a media frenzy and ignited what became known as the "love triangle" era, a chapter Aniston hasn’t forgotten.

In an interview with Vanity Fair published on August 11, 2025, Aniston discussed the intense media scrutiny that followed her separation from Pitt. Reflecting on the tabloids' portrayal of the situation, she said, “It was such juicy reading for people. If they didn’t have their soap operas, they had their tabloids.”

She continued, "It’s a shame that it had to happen, but it happened. And boy did I take it personally.”

At the time of their split, Aniston was navigating the fallout while Pitt quickly moved on with Jolie. In fact, the same year they parted ways, Pitt and Jolie posed for a now-infamous photo shoot for W Magazine, showing the couple in a domestic scene, depicting a married life with children.

The shoot was a pivotal moment in their relationship, which eventually led to their marriage in 2014. After two years, Jolie filed for divorce, sparking a lengthy legal battle.

When speaking about her emotional state during that period, Aniston explained, “Just pick yourself up by the bootstraps and keep on walking, girl.”

Aniston also recalled a 2005 interview with Vanity Fair in which she had candidly expressed her feelings about the photos of Pitt and Jolie. "The world was shocked, and I was shocked. I'd be a robot if I said I didn't feel moments of anger, of hurt, of embarrassment," Aniston said.

She also noted, "He makes his choices. He can do—whatever. We're divorced, and you can see why."

Despite the media circus, Aniston emphasized the complexity of her relationship with Pitt, stating, "I love Brad; I really love him. I will love him for the rest of my life. He's a fantastic man. I don't regret any of it, and I'm not going to beat myself up about it. We spent seven very intense years together; we taught each other a lot—about healing, and about fun. We helped each other through a lot, and I really value that. It was a beautiful, complicated relationship."

By 2008, Aniston had begun to move forward, telling Vogue, "Well, it never was that bad... I can't even remember the darkness. I mean, in the end, we really had an amicable split. It wasn't mean and hateful."

She also shared that soon after their separation, they had a "long, long conversation" and had been on good terms ever since.

Pitt, too, had spoken about his past with Aniston in 2011. In a Parade interview, he explained that he felt his marriage to Aniston was part of the reason he wasn't living the fulfilling life he desired.

He later clarified his comments, saying, "Jen is an incredibly giving, loving, and hilarious woman who remains my friend. It is an important relationship I value greatly."

In 2015, Aniston further discussed her feelings on the divorce during an appearance on CBS Sunday Morning. “I don't find it painful... We've exchanged good wishes and all that sort of stuff to each other, but not a constant thing,” she remarked.

She also expressed frustration over the media's obsession with their past, saying, "If the world only could just stop with the stupid, soap opera bulls**t. There's no story."

As Aniston's life moved forward, she married Justin Theroux in 2015, only to divorce in 2018. Reflecting on her relationships, Aniston noted in Elle that her marriages were "very successful" in her opinion.

She explained, "When they came to an end, it was a choice that was made because we chose to be happy, and sometimes happiness didn’t exist within that arrangement anymore.”

Despite the end of their marriage, Aniston and Pitt have remained cordial. In 2020, their brief reunion at the SAG Awards garnered plenty of attention, with Pitt joking that their encounter was likely to be "the second most important reunion of her year." He also shared, “I’ll run into Jen... She’s a good friend.”

By 2021, Aniston confirmed that there was no lingering tension between them. “It was absolutely fun,” she said, reflecting on their friendly interactions at the SAG Awards and the Fast Times at Ridgemont High virtual table read.

Aniston also put to rest rumors from 2022, particularly those suggesting that her divorce from Pitt was because of her decision not to have children. She asserted, “And God forbid a woman is successful and doesn't have a child,” explaining that the narrative surrounding their divorce was based on falsehoods.

Though Aniston’s personal life has evolved, her thoughts on her time with Pitt and Jolie remain candid, with the actress acknowledging that their past, no matter how challenging, was a formative part of her journey. And while the "love triangle" era may have dominated headlines for years, Aniston has clearly put that chapter behind her, with a focus on moving forward with grace and clarity.

Featured image credit: Barry King / Getty

Brad Pitt has spoken publicly for the first time about his divorce from Angelina Jolie.

Brad Pitt has opened up about his divorce. Credit: Rebecca Sapp / Getty

Brad Pitt, 61, and Angelina Jolie, 49, were once Hollywood’s most A-list couple.

From co-stars to parents to business partners, their relationship unfolded on the world stage... before crumbling just as publicly.

Their romance began on the set of Mr. & Mrs. Smith in 2004, while the Fight Club star was still married to Jennifer Aniston. Though the pair denied any infidelity, both later admitted they fell in love during filming.

Pitt divorced Aniston in 2005, and soon after, he and Jolie confirmed their relationship, quickly becoming tabloid royalty as “Brangelina.”

Brad Pitt and Angelina Jolie were once Hollywood's A-list couple. Credit: Kevin Mazur / Getty

Over the years, the former couple expanded their family to six children - Maddox, Pax, Zahara, Shiloh, and twins Knox and Vivienne - and married in 2014. But just two years later, Jolie filed for divorce in 2016 following an alleged altercation on a private flight.

The fallout triggered a long, highly public legal battle involving custody and a jointly owned French vineyard.

Now, nearly eight years later, that legal fight has finally come to an end. In an interview with GQ published May 28, Pitt addressed the finalization of their divorce for the first time.

"I don't think it was that big of a deal," he shared. "It was just something that came to an end. Legally."

Despite the prolonged public scrutiny, the Troy star said he feels at peace. A source close to the actor shared that he’s “happy that the divorce is now a thing of the past” and is content in his relationship with Ines de Ramon, whom he’s been dating since 2022.

"It's been in the news for 30 years, brother. Or some version of my personal life," Pitt said. These days, he described his life as "contained" and "secure" with close friends and loved ones.

On Jolie’s side, a lawyer confirmed the actress is relieved. “Angelina is exhausted, but relieved that this part is over,” they said, per the Evening Standard.

Before his time with the Maleficent actress, Pitt’s marriage to Aniston defined early-2000s celebrity culture. The two were married from 2000 to 2005, splitting just as Friends wrapped its final season.

At the time, they issued a joint statement dismissing tabloid rumors, insisting the decision was made with “great love and admiration.” But speculation about Pitt’s growing bond with Jolie dominated headlines.

In hindsight, Pitt’s honesty about his feelings helped avoid further drama. Jennifer’s close friend and Friends co-star Courteney Cox later shared that he was upfront with Aniston.

“I don’t think he started an affair physically, but I think he was attracted to her,” Cox told Vanity Fair. “There was a connection, and he was honest about that with Jen. Most of the time, when people are attracted to other people, they don’t tell. At least he was honest.”

The emotional toll came at a vulnerable moment for Aniston, who was navigating the end of her iconic TV role while her marriage dissolved. One insider told The Mirror: “They gradually lost sight of themselves as individuals. Despite their nice lifestyle and having everything they might want, they weren’t happy.”

Years later, the Just Go With It star firmly rejected the media’s portrayal of her as the heartbroken ex in a feud with Jolie.

“I think it's time people stop with that petty B.S. and start celebrating great work,” she told Entertainment Tonight, calling the narrative “tiresome and old, like an old leather shoe.”

The couple were married from 2000 to 2005. Credit: Barry King / Getty

With the legal chapter of his relationship with Jolie finally closed, Pitt is focusing on the future.

His forthcoming film F1, where he stars as a Formula 1 driver opposite Damson Idris, hits theaters on June 27 and marks a new phase in his professional journey.

Featured image credit: Laurent KOFFEL / Getty

Angelina Jolie has opened up in stark new detail about the emotional and financial toll of her split from Brad Pitt.

Jolie, 50, and Pitt, 61, became one of Hollywood’s most talked-about couples after meeting on the set of Mr. & Mrs. Smith in 2005.

They married in 2014 at Château Miraval, the French estate they purchased together, and share six children.

But just two years after their wedding, the Maleficent star filed for divorce in 2016, citing irreconcilable differences.

The divorce was finalized in 2024, though their legal entanglements are far from over.

Miraval Tied to ‘Difficult and Traumatic’ Chapter

In a new court filing submitted on Monday in Los Angeles, Jolie described the emotional weight Château Miraval still carries.

As the former couple continues to fight over the winery’s ownership, the Lara Croft actress said the estate is inextricably linked to the breakdown of their family.

“The events leading to my need to separate from my ex-husband were emotionally difficult for me and our children,” she said in her declaration, per Page Six.

She added that neither she nor the children, Maddox, 24; Pax, 21; Zahara, 20; Shiloh, 19; and twins Knox and Vivienne, 17, have returned to the château since the split.

“Post-separation, I immediately began to look for a new house for me and our children, initially renting a home while looking for a more stable solution,” she wrote.

Finances, Family, and Emotional Fallout

The Maria star claimed her savings were tied up in the winery and that she hadn’t asked Pitt for alimony or financial support, choosing instead to take two years off work to focus on her children’s recovery.

“I was also very concerned about the health of our children,” she said, noting that Pitt allegedly agreed to loan her money “with interest”.

In 2017, she attempted to sell her share of Miraval to the Fight Club actor, but she said the conversations were fraught with emotional strain.

“Miraval was one of the first major investments we made together, and it was a focal point of our family life,” she said. “We were married there, I spent part of my pregnancy there and I brought our twin children home there from the hospital. To have such a sudden break from my home and memories has been hard, and it was especially difficult for the children to have their lives so disrupted.”

The NDA Dispute and Sale to Stoli

By 2021, Jolie claimed her ex-husband demanded she sign a non-disclosure agreement before he would buy out her share of Miraval.

She refused, saying there was “no practical need for the NDA,” as she had not spoken publicly about the alleged abuse that led to their divorce, USA Today reported.

“As the mother of our children, as well as an advocate for victims of violence around the world, I found his demand extremely painful,” she wrote.

After the deal collapsed, Jolie sold her shares to Stoli Group, prompting Pitt to sue. His legal team called the sale unlawful, while Jolie’s countersuit argues there was no agreement requiring mutual consent for a sale.

Her lawyers claim Pitt pulled out of the deal after she submitted sealed evidence of domestic violence during their custody dispute.

The dispute has escalated into a discovery fight, with Pitt requesting Jolie’s private messages and communications with her legal team. Jolie’s lawyers are pushing back, calling the motion “without any legal basis” and a continuation of Pitt’s “efforts to control Angelina.”

Jolie is now seeking $33,000 in attorneys’ fees for responding to Pitt’s request.

In one redacted communication included in the court filing, Jolie wrote: “I need to remove all stress. I honestly feel I am getting sick from worry. So, I would like us to discuss better support and not continuing relationships that you see cause me stress."

Featured image credit: Kevin Mazur / Getty

Brad Pitt's "confession" to Jennifer Aniston about Angelina Jolie before they officially divorced has been revealed.

Aniston, 56, and Pitt, 61, tied the knot in July 2000 and enjoyed five years of marriage before announcing their separation in January 2005.

In a joint statement, the couple explained that their divorce was "not the result of any of the speculation reported by the tabloid media".

"This decision is the result of much thoughtful consideration. We happily remain committed and caring friends with great love and admiration for one another," they added.

At the time, rumors quickly swirled that the Fight Club actor had fallen for his Mr. & Mrs. Smith co-star, Angelina Jolie.

While the pair denied any physical affair while Pitt was still married, they admitted they fell in love during filming. Shortly after the divorce, they confirmed their relationship, launching the era of “Brangelina".

However, it wasn't until later that a pivotal moment between Pitt and the Friends actress came to light.

According to The Morning Show star's long-time friend and co-star Courteney Cox, Pitt had been transparent with Aniston about his feelings for Jolie.

“I don’t think he started an affair physically, but I think he was attracted to her,” Cox said in a 2005 interview with Vanity Fair. “There was a connection, and he was honest about that with Jen.

"Most of the time, when people are attracted to other people, they don’t tell. At least he was honest about it. It was an attraction that he fought for a period of time," she added.

While the confession may have spared Aniston from finding out through tabloids, it came at a time when she was already going through a difficult personal chapter.

With Friends ending in 2004, sources close to the couple suggested she was navigating a transitional period while Pitt was away filming. Per The Mirror, one insider shared: "They gradually lost sight of themselves as individuals. And despite their nice lifestyle and having everything they might want, they weren't happy. They lost a sense of self."

Following the split, the Just Go With It actress was frequently cast by the media as the heartbroken ex, caught in an alleged rivalry with Jolie. But ten years later, she dismissed those narratives with poise.

"I think it's time people stop with that petty B.S. and start celebrating great work and stop with the petty kind of silliness," Aniston told Entertainment Tonight, adding that the fixation on the Jolie-Aniston dynamic is "tiresome and old," like "an old leather shoe".

Pitt and Jolie eventually married in 2014 but divorced in 2016 after two years. Their separation led to a protracted legal battle over custody of their six children - Maddox, Pax, Zahara, Shiloh, and twins Knox and Vivienne - as well as disputes over a jointly owned vineyard.

Meanwhile, Aniston has continued to focus on her career and privacy, rarely engaging with the ongoing commentary surrounding her past relationships.

Featured image credit: Barry King / Getty

Like most of you, I was pretty devastated to learn that Angeline Jolie and Brad Pitt were getting a divorce after two years of marriage, but six kids and a whole lot of history. Celebrity relationships on the whole feel hollow and short-lived, and in a year where we'd already lost the likes of Alan Rickman, Prince and David Bowie, we just wanted something to believe in. We did not get it in Brangelina.

But longtime fans of Brad Pitt may not have been so surprised; a little over a decade earlier, a similar breakup had occurred, which sent similar shockwaves across the showbiz world. So, back in the year 2000, Brad Pitt married a little-known sitcom actress by the name of Jennifer Aniston. No worries if you've never heard of her.

But then, Pitt met Jolie on the set of Mr and Mrs Smith in 2004, and soon, Brad Pitt and Jennifer Aniston split, and Brad Pitt soon shacked up with Angelina Jolie. It's no secret that Jolie had a huge part to play in the eventual breakup of Brad and Jen, but as the dust settles on her own relationship with Pitt, Jolie has opened the lid on her feelings over Jennifer Aniston.

After being involved in one of the highest-profile celebrity breakups of the early 2000s, you'd forgive Angelina Jolie for a little bit of guilt at playing homewrecker, but a source close to Jolie says that nope: Jolie still has no bad feelings over what happened with Jennifer Aniston.

[[instagramwidget||https://www.instagram.com/p/BosmbLXBN5f/?taken-by=joliepittsofficial]]

"Angelina has many regrets after leaving Brad, but one thing she has never felt terrible about was any bad feelings Jen Aniston may have towards her," says the source, but while it sounds a little bit harsh, can you really blame her? Brad, after all, remained faithful to Jennifer Aniston until the pair split.

Jolie did admit in 2006, however, that there had been feelings that weren't acted on for a while concerning Brad Pitt and Angelina Jolie - they'd reportedly fallen for each other all the way back in 2004 - Aniston and Pitt divorcing in 2005.

Jolie, however, did have a few regrets with her now ex-husband following their long relationship together, revealed the source. Turns out, she had bigger fish to fry than to be too concerned about how Brad's ex was taking the whole thing. Which is fair enough, I guess.

"Angelina wonders how she could have communicated with Brad more, or how she could have helped him battle his demons better. So many things Angelina questions and/or feels regretful about concerning their relationship still haunt her, but she never worries about how her relationship or divorce may have affected Jen. Angelina simply never really worries or ever really thinks about Jen."

[[instagramwidget||https://www.instagram.com/p/BoxA-BxhwM8/?utm_source=ig_embed]]

When we talk about Angelina Jolie and Jennifer Aniston, maybe it's a lot more appealing to think of them as two women fighting over the same hunk. But talking to both of them about their relationships with Brad Pitt, Jolie and Aniston seem to want to put it all behind them. Can't blame them, really.