Fans were often left speculating about the reasons behind the breakups of famous couples, especially when it came to unexpected pairings. One such surprising duo was Julia Roberts and Matthew Perry, whose brief relationship in the 1990s made headlines.

Though it might seem unlikely, the two were romantically linked after Julia guest-starred on Friends in 1995. Fans were curious about why the couple split, but answers were elusive—until Matthew Perry recently revealed the details in an interview with The Times.

According to Perry, he was the one who initiated the breakup, despite his deep affection for Roberts. Their connection began when the Pretty Woman star was invited to appear on Friends, with the condition that her storyline would be tied to Perry’s character. To win her over, Perry sent her a bouquet of red roses and a note that read, “The only thing more exciting than the possibility of you being on the show is knowing I can now send you flowers.”

At the time, Roberts was a major film star, but despite the distance between them, the pair started exchanging letters. After months of writing, Roberts returned to Los Angeles, and the two began dating. However, despite their budding romance, Perry’s insecurities led him to end the relationship.

In his memoir, Perry admitted he struggled with feelings of unworthiness. “It was impossible to be in a relationship with Julia Roberts,” he explained. “I was convinced she would break up with me. I thought I wasn’t good enough or attractive enough.”

He ultimately decided to end things to avoid the heartbreak he believed was inevitable, saying, “I broke up with the beautiful and brilliant Julia Roberts so she wouldn’t break up with me first.”