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Friends fans likely remember when Julia Roberts guest-starred alongside Matthew Perry. Perry and Roberts later went on to date, though their relationship reportedly didn’t last long. And Perry said Roberts looked incredibly confused when he pulled the plug on the relationship.

Julia Roberts allegedly looked confused when Matthew Perry dumped her

Julia Roberts and Matthew Perry dated in 1996, though their relationship reportedly only lasted about two months. Perry explained his brief romance in his memoir, Friends, Lovers and the Big Terrible Thing.

According to Perry, Roberts only wanted to guest-star in Friends if she could participate in a storyline with Chandler Bing. In anticipation of her temporarily joining the show, Perry purchased 36 roses to send to Roberts. “The only thing more exciting than the prospect of you doing the show is that I finally have an excuse to send you flowers,” he wrote in a card with the flowers, according to Harper’s Bazaar.

Before Perry and Roberts officially worked together in Friends, they engaged in three months of faxing back and forth. “I was so excited that some nights I would find myself out at some party sharing a flirtatious exchange with an attractive woman and cut the conversation short so I could race home and see if a new fax had arrived,” he wrote. “Nine times out of 10, one had.”

When they finally got together, they dated for just two months before Perry called it quits. He wrote in his memoir that he felt “constantly worried” that she’d break up with him. “I was not enough; I could never be enough; I was broken, bent, unlovable,” he wrote. “So, instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts.”

Perry wrote that Roberts had a “look of confusion on her face” when he ended the romance. “She might have considered herself slumming it with a TV guy, and TV guy was now breaking up with her.”

Julia Roberts called the ‘Friends’ star ‘awfully clever’

Jennifer Aniston, Courteney Cox, Matt LeBlanc, Lisa Kudrow, Matthew Perry, and David Schwimmer from 'Friends' on the red carpet
The ‘Friends’ cast on the red carpet | Jim Smeal/Ron Galella Collection via Getty Images
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Old interviews show Julia Roberts complimenting her Friends co-star, Matthew Perry. “I was very nervous because he’s awfully clever, and funny, and handsome, and I was just nervous,” Roberts said in an interview.

During another interview with Entertainment Tonight, Roberts said she felt like she could “maybe die or throw up” with how nervous she was to star alongside Perry. ” … It’s a little bit like coming into a 90-day movie shoot on day 88,” she said. “These people all know each other, they all know their characters, they know how to be funny.”

At the time, Perry called Roberts an “amazing person.”

“She’s everything every guy thinks she is,” Perry told an interviewer.

Matthew Perry notoriously had cold feet in his relationships

Julia Roberts wasn’t the only high-profile woman that Matthew Perry broke up with. Unfortunately, the actor had cold feet several times, breaking up with many women.

“Matthew always dreamed of having the perfect family,” a source told Daily Mail. “He wanted a wife and at least a couple of kids. And he said he wouldn’t even mind marrying a woman who already had kids.”

“Matthew dated dozens of women, but, in the end, he always felt they were only interested in his money and his fame,” the source continued. “And he was generous to a fault. He would shower women with gifts only to have them pack up their goodies and walk away.”

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