Brad Pitt, Jennifer Aniston & Angelina Jolie Love Triangle Explained | Mr. & Mrs. Smith Timeline

Few Hollywood relationships have generated as much fascination, or as many competing narratives, as those involving Brad Pitt, Jennifer Aniston and Angelina Jolie. Pitt and Aniston were one of Hollywood’s most recognizable couples when they separated in 2005, amid intense speculation about Pitt’s connection with his Mr. & Mrs. Smith co-star Jolie.

What followed became far bigger than an ordinary celebrity breakup. Photographs from Kenya, the controversial “Domestic Bliss” spread in W Magazine, the rise of “Brangelina” and the media-driven “Team Aniston versus Team Jolie” rivalry made it one of the defining celebrity stories of the 2000s. Here is the timeline behind the relationships, rumors, and events that shaped the saga.

Brad Pitt And Jennifer Aniston: Marriage And the 2005 Split

Before the headlines, rumors, and Hollywood drama, Brad Pitt and Jennifer Aniston were the couple everyone wanted to believe in. They began dating in 1998 after being introduced by their managers, and their romance quickly became one of the most closely watched relationships in the entertainment industry. Aniston had become a household name through Friends, while Pitt was already one of Hollywood’s biggest heartthrobs, making their pairing feel like a perfect collision of television fame and movie-star glamour.

Their relationship reached another level when they married on July 29, 2000, in a private Malibu ceremony. For the next several years, Pitt and Aniston were one of Hollywood’s most recognizable couples, maintaining a high-profile presence while largely keeping their private life out of the spotlight. Pitt even appeared as Will Colbert, Rachel Green’s former schoolmate, on Friends in 2001.

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In 2001, Pitt and Aniston also helped establish Plan B Entertainment alongside producer Brad Grey and executive Kristin Hahn. Pitt retained control of the production company following the couple’s divorce.

Brad Pitt, Angelina Jolie and Mr. & Mrs. Smith: The 2005 Timeline

The timeline surrounding Pitt, Aniston and Jolie soon became one of the most closely examined celebrity stories of the decade.

Pitt and Jolie met while filming Mr. & Mrs. Smith in 2004, when Pitt was still married to Aniston. Their on-screen chemistry fueled widespread speculation, although neither publicly confirmed a romantic relationship during production. Jolie later said they developed feelings for each other while working together, but both maintained that Pitt did not become romantically involved with her until after he and Aniston had separated. Jolie’s pregnancy with Pitt’s child was confirmed in January 2006, publicly establishing them as a couple.

In January 2005, Pitt and Jennifer Aniston announced their separation, setting off a media frenzy that soon placed all three stars at the center of a worldwide tabloid obsession.

The timeline only grew more dramatic in the months that followed. Aniston filed for divorce in March, while photos of Pitt and Jolie together in Kenya emerged in April, shortly before Mr. & Mrs. Smith hit theaters and became a major box-office success. By September, Aniston gave her much-discussed Vanity Fair interview, addressing the painful breakup and the media narratives surrounding it. Pitt and Aniston’s divorce became official on October 2, 2005, formally ending their marriage after five years.

The “Domestic Bliss” W Magazine Photos and Team Aniston vs. Team Jolie

In July 2005, W Magazine published its now-famous “Domestic Bliss” portfolio, photographed by Steven Klein and created in collaboration with Pitt. The 60-page spread depicted Pitt and Jolie playing a fictionalized suburban family in Palm Springs, complete with children gathered around their imagined home. Because the shoot appeared only months after Pitt and Aniston’s separation and while Pitt and Jolie had not publicly confirmed their relationship, it became another major flashpoint in the media frenzy.

The “Team Aniston” and “Team Jolie” divide soon became shorthand for the competing narratives surrounding the breakup. Much of the coverage framed Aniston as the relatable, wronged wife and Jolie as the unconventional Hollywood outsider, encouraging audiences to choose a side. That framing turned a private relationship breakdown into a larger pop-culture debate and helped make the story one of the defining celebrity media phenomena of the mid-2000s.

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Looking back, one of the most striking aspects of the story is how aggressively the media reduced three real people to characters in a public drama. Aniston became the “wronged wife,” Jolie the “other woman,” and audiences were encouraged to choose a team. The episode remains culturally fascinating, but it also demonstrates how easily celebrity relationships can be turned into entertainment before the public knows what happened privately.

From “Brangelina” to the Château Miraval Lawsuit

The story didn’t end when Brad Pitt and Jennifer Aniston’s divorce became official. Instead, the 2005 scandal grew into something much bigger as Pitt and Angelina Jolie became “Brangelina,” one of Hollywood’s most famous power couples, before their own relationship eventually collapsed under intense public and legal scrutiny. More than two decades later, the fallout has continued through the bitter Château Miraval dispute, showing just how long the shadow of that original scandal has lasted.

After their relationship became public, Pitt and Jolie embraced their status as a global celebrity family, often controlling how their personal lives were publicized while supporting charitable causes. They held their wedding celebration at Château Miraval in 2014. The couple began leasing the French estate in 2008 and later purchased it, with reputable reports placing the acquisition in 2011 or 2012. Jolie filed for divorce in 2016, beginning years of litigation involving custody and shared assets. A judge declared Pitt and Jolie legally single in 2019, but the remaining terms of their divorce were not settled until December 2024. Their separate dispute over Château Miraval remains unresolved.

The winery dispute, often called the “War of the Rosé”, centers on Jolie’s 2021 sale of her Château Miraval stake to Tenute del Mondo, the wine division of the Stoli Group. Pitt alleges that the sale violated an agreement requiring the approval of both parties to any transfer of ownership; Jolie denies that such an agreement prevented the sale. Her attorneys have also argued that negotiations over Pitt's purchase of her stake broke down because of a proposed nondisclosure agreement.

The case remains active in 2026. In June, a California court granted Pitt’s request to compel depositions from members of the Stoli Group. In August, his lawyers renewed their attempt to obtain Jolie’s financial and property records, arguing that information about her income could be relevant to the circumstances surrounding the sale. Jolie’s attorneys opposed the request. Court scheduling information reported in June indicated that a trial was expected in August 2027.

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Perhaps the biggest change has been the way the story is remembered. In 2005, coverage often reduced Aniston and Jolie to opposing sides and encouraged fans to pick a favorite. Aniston eventually moved beyond the “wronged woman” narrative, while the later disputes between Pitt and Jolie added layers that were impossible to capture in the simple “Team Aniston vs. Team Jolie” framing. The saga also offers an early example of the celebrity culture that social media later amplified, where relationship rumors, paparazzi images, fan loyalties, and private family disputes can become part of a much larger public conversation.

Did Brad Pitt cheat on Jennifer Aniston with Angelina Jolie?

No publicly verified evidence has conclusively established when Pitt and Jolie’s relationship became romantic. Jolie later acknowledged that they developed feelings while filming Mr. & Mrs. Smith, but Pitt and Jolie maintained that their romantic relationship began after Pitt and Aniston separated.

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