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“I could never be enough, I was unlovable”: Julia Roberts’ Ex-boyfriend Dumped Her Because He Was Insecure of Dating $250 Million Rich Hollywood Star

The biggest rom-com star of the '90s, Julia Roberts, once fell in love with a man of a far more modest station than her. But unlike those movies of hers, it did not end with a happily ever after. The last decade of the 20th century defined Hollywood's ability to churn out extravagantly celebrated and all-time-favorite rom-coms, ranging from Pretty Woman and Runaway Bride to Sleepless in Seattle and You've Got Mail.

Julia Roberts has dominated our big screens (alongside the evergreen Meg Ryan, of course) and nurtured our unrealistic expectations of love and romance with her Hollywood filmography. It was only a matter of time until she would find herself a Notting Hill-worthy romance.

Julia Roberts Gets Her Heart Broken By F.R.I.E.N.D.S. Alum

Breaking up with Julia Roberts – could he BE any more stupid? As it turns out, the Eat, Pray, Love star ended up falling for the one person from the cast of the popular '90s sitcom, F.R.I.E.N.D.S. who could not be the boy she could stand in front of, asking him to love her. In his recently released memoir, Friends, Lovers, and the Big Terrible Thing, Matthew Perry reveals his arduous battle against addiction and how it ended up costing him the most wonderful romance of the decade.

"Dating Julia Roberts had been too much for me. I had been constantly certain that she was going to break up with me. Why would she not? I was not enough; I could never be enough; I was broken, bent, unlovable. So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts. She might have considered herself slumming it with a TV guy, and TV guy was now breaking up with her."

Matthew Perry goes on to reveal how the actress was taken aback by the break-up – "I can't begin to describe the look of confusion on her face." Considering how Perry would not go on to win his battle against substances completely until almost a decade later, the break-up, on his part, almost presents itself like a cry for help on one hand, and on the other, the most self-less act of love toward Roberts and the kind of love that she deserved that Perry stopped to consider in a moment of clarity. Mostly though, it was the latter's undeniable insecurity that ended up splitting the couple apart.

The Extraordinary Romance of Julia Roberts and a TV Guy

It would almost sound unbelievable at first if Chandler Bing just walked onto the set one day and announced he was seeing Julia Roberts. But, in Hollywood, nothing is too fantastical to be true. So when the goddess of Hollywood and rom-com royalty herself asked to pursue Matthew Perry, the ensuing months that followed were total and utter chaos.

"Marta Kauffman approached me and said that I should probably send flowers to Julia Roberts. You mean the biggest-star-in-the-universe Julia Roberts? 'Sure, great, why?' I said. Turned out Julia had been offered the post–Super Bowl episode in season 2 and she would only do the show if she could be in my storyline. Let me say that again—she would only do the show if she could be in my storyline. (Was I having a good year or what?). But first, I had to woo her."

As it turns out the wooing consisted of three dozen roses from Perry, "bagels — lots and lots of bagels" from Roberts, and a thesis paper on quantum physics, wave-particle duality, and the uncertainty principle and entanglement as per the latter's request. Their romance, however short-lived, was an extraordinary one, and if it had survived the F.R.I.E.N.D.S. alum's struggle with addiction, would have definitely been more phenomenal than Julia Roberts' own filmography.

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