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Matthew Perry: Why I’ve broken up with every ‘wonderful’ woman I’ve dated

His love life was DOA.

Matthew Perry says he pulled the plug on nearly every relationship he ever had because of personal insecurities.

“I break up with them because I’m deathly afraid that they will find out that I’m not enough, that I don’t matter, and that I’m too needy, and they’ll break up with me and that will annihilate me and I’ll have to take drugs and that will kill me,” the “Friends” star, 53, confessed to GQ on Thursday ahead of the release of his new memoir, “Friends, Lovers and the Big Terrible Thing.”

“That’s why I break up with these wonderful women that have crossed my path.”

Perry seemingly regrets calling it quits too early with many of these women, noting that there are 10 women “on the face of the planet” whom he would “kill to be married to,” but they have moved on and are married with kids.

Matthew Perry on a red carpet.
Matthew Perry was “deathly afraid” that the “wonderful” women he dated would want to break up with him. WireImage

“And you’re not supposed to look in the rearview mirror because then you’ll crash your car,” he added. “But I looked in the rearview mirror and I was like, they’re all gone. They’re all happy, which is great, but I’m the one who’s sitting in a screening room by myself. And there’s no lonelier moment than that.”

Perry also shared with the magazine that he was only ever dumped once and that the experience caused him to spiral for years.

“I lit candles in my house and drank and drank and drank over that, for about two years,” the “Fools Rush In” star said.

Matthew Perry sitting in a chair on a patio.
Perry told GQ it would “annihilate” him if he got broken up with first. Ryan Pfluger/GQ

Although Perry did not go into detail about all of his relationships that failed, he did open up about how his romance with Julia Roberts came to an abrupt end.

The sitcom legend said he and the “Pretty Woman” star, now 54, spent an amazing New Year’s Eve together in Taos, NM, in 1995 — which is a day he wishes he could “live over and over again” — but eventually ended their relationship for the same reason others did.

“We were driving in a car and being chased by paparazzi,” he explained, “and I said, ‘I want to break up with you.’ Because I think she fancied herself slumming it with TV Boy.”

Perry added, “And then TV Boy just broke up with her. And you know that the reason I did that was purely out of fear. I needed to get out.”

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Matthew Perry and Julia Roberts laughing together on "Friends."
Some of Perry’s exes include Julia Roberts, Lizzy Caplan and Neve Campbell.©Warner Bros/Courtesy Everett C
Matthew Perry and Lizzy Caplan talking at a sporting event.
Some of Perry’s exes include Julia Roberts, Lizzy Caplan and Neve Campbell.SplashNews.com
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Matthew Perry and Neve Campbell at the "Three to Tango" premiere.
Some of Perry’s exes include Julia Roberts, Lizzy Caplan and Neve Campbell.WireImage
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The “17 Again” star said Roberts seemed confused and “upset,” and the two haven’t run into each other since.

“The reason I broke up with her is out of sheer fear,” he reiterated. “I was like, she’s going to dump me any minute, so I should probably dump her first. And that was fear-based and probably stupid. But that’s what I did.”

Perry’s most recent relationship was to literary manager Molly Hurwitz, who is more than 30 years his junior. The pair got engaged in November 2020 but called it quits for good less than a year later.