Matthew Perry’s Friends sitcom went super popular back in 1994, and the world fell in love with the entire cast – so much so that the already 10 seasons TV show even called for a reunion! But what became more famous and talked about was the actor’s love life behind the scenes, with none other than the Pretty Woman actress, Julia Roberts.

Matthew Perry and Julia Roberts

But while their relationship didn’t last long due to a rather foolish reason given by the Friends star, the Perry-Roberts relationship was a much talked about topic at the time, judging how it made its way to even Howard Stern’s show, where the host didn’t step back from brutally humiliating the already insecure Matthew Perry.

Matthew Perry’s Colossal Relationship ‘Disaster’ With Julia Roberts

Crazy in Love: Julia Roberts with Matthew Perry

Back when Friends was still in filming, Matthew Perry found himself a new flame – Julia Roberts and their love life wasn’t that of the ordinary. The Chandler Bing portrayer first sent flowers to her and exchanged messages on fax with her to allure her and get her on the sitcom’s season 2.

But little did he know that he would soon find himself enchanted enough to be in a romantic relationship with the Pretty Woman star. He even wrote in his memoir, Friends, Lovers, and the Big Terrible Things, about her.

“Somewhere in the world, there is a stack of faxes about two feet long — a two-foot-long courtship, filled with poems and flights of fancy and two huge stars falling for each other and connecting in a beautiful, romantic way.”

His invitation was followed by Roberts’ condition that she would join if he explained ‘quantum physics’ to her. Thus began their ‘three-month-long courtship by daily faxes’, where Perry would find himself sitting by his fax machine and exchanging hundreds of messages with the actress, never getting enough of her.

This went on until a little after the Notting Hill actress starred in the show, after which the Friends star went into a lot of self-doubts about him not being enough for her, and that he was ‘broken, bent, and unlovable’.

Thus, trapped in his own head and insecurity, Matthew Perry broke up with Julia Roberts, leaving her confused as to what went wrong and ending their pure-as-poetry relationship in a colossal disaster.

Howard Stern Brutally Humiliated Matthew Perry Over His Breakup With Julia Roberts

Howard Stern brutally humiliated Matthew Perry for breaking up with Julia Roberts the way he did

A little after their breakup, his Friends co-star, David Schwimmer, appeared on The Howard Stern Show in 1998. That’s when the topic of Matthew Perry and Julia Robert’s devastatingly disastrous relationship surfaced. Brutually humiliating the already insecure star, Howard Stern said,

“What is he on, acid? What is Matt Perry on anyways? He wasn’t even on anything that cleft [like heroin, crack], he was on counter medication. Cough syrup or something. What was he on, pills? I don’t know.”

To this, an embarrassed David Schwimmer responded by saying that it was ‘a painkiller’. Nonetheless, Perry’s reason for breaking up with the Ticket to Paradise actress was a one-sided decision that could’ve changed had he talked it out.