The high-profile marriage between Jennifer Aniston and Brad Pitt didn’t just shake Hollywood—it also left a deep emotional scar on Gwyneth Paltrow. Close sources revealed that she was so upset, she once told Pitt’s friends something that left them speechless.

Back in the mid-1990s, Gwyneth Paltrow and Brad Pitt were one of the most celebrated couples in the entertainment world. Having met on the set of the thriller Se7en in 1994, their chemistry quickly translated off-screen. The two stars were seen as a golden couple—attractive, talented, and seemingly perfect together. They got engaged in 1996, sparking widespread speculation about a wedding. However, just a year later, in 1997, the engagement was called off without a clear explanation, leaving fans and media puzzled.

Years later, in a moment that many now see as a revelation of lingering heartbreak, Paltrow’s reaction to Pitt’s next major relationship told a deeper story. In a resurfaced interview during the 2000 Toronto International Film Festival, when asked about Pitt’s marriage to Jennifer Aniston just two months earlier, Paltrow responded with an expression that was described as “mang hình viên đạn”—a stare like a bullet. “You really want to ask me that?” she replied coldly. “I can’t comment on that.” Her curt response masked what insiders would later reveal was quiet devastation.

According to excerpts from a new biography by O’Dell, Paltrow confided in friends that she was deeply saddened by Pitt’s engagement to Jennifer Aniston. She even made a striking comment, reportedly saying Brad Pitt “has no taste in women”—a jab that, while harsh, reflected her emotional turmoil. During a private dinner with Aerin Lauder, heiress to the Estée Lauder cosmetics empire, Paltrow allegedly voiced sharp criticism of her former fiancé. Friends at the time noted that she was struggling to cope with what felt like emotional rejection.

This heartbreak may have been rooted not just in lost love, but in Gwyneth’s own doubts during the relationship. While filming Emma, she admitted to a crew member that she wasn’t sure Brad was truly compatible with her, even confessing that she had a growing affection for another actor—Hugh Grant. “Brad and I were raised so differently,” she said in a later interview. Despite their affection, the couple had irreconcilable differences in background and outlook. That distance eventually eroded the foundation of their bond.

By the time Brad Pitt proposed to Jennifer Aniston in 1999 and married her in a lavish Malibu ceremony in July 2000, Gwyneth had already moved on publicly—but not, perhaps, emotionally. Though she began dating Ben Affleck in 1997, that relationship was far from stable. The actor, as noted in the same book, was struggling with alcohol and gambling issues at the time. Their romance eventually fizzled out after more than a year.

Meanwhile, Pitt’s marriage to Aniston, though glamorous on the surface, ended in 2005 following his highly publicized connection with Angelina Jolie, his co-star in Mr. & Mrs. Smith. That affair would later become one of the most talked-about scandals in Hollywood history. Ironically, Pitt’s seemingly perfect marriage with Aniston mirrored what many had once believed he would share with Paltrow.

Gwyneth eventually found stability and a new chapter with Coldplay frontman Chris Martin. The two married in 2003 and had two children—Apple and Moses—before divorcing in 2014. Her second marriage, to producer Brad Falchuk in 2018, appears to be more grounded and private. In contrast, Pitt’s romantic life has continued to draw headlines, particularly his tumultuous relationship with Angelina Jolie, which ended in a contentious divorce finalized in 2019.

Despite the years that have passed, Gwyneth Paltrow’s emotional scars from her relationship with Brad Pitt are still evident in the ways she’s referenced it in various interviews. The rawness of her reaction to his marriage with Jennifer Aniston remains a telling sign of just how deep the wounds went. Though she has found happiness and fulfillment in other aspects of life, the ghost of that high-profile romance still lingers—proof that even Hollywood’s brightest stars are not immune to heartbreak.