Had 'Elaborate Fantasies' About Them Running Away Together

Late Friends star Matthew Perry was very open about his feelings for one of his co-stars. He spoke of his “elaborate fantasies” about them running away together in his autobiography, Friends, Lovers and the Big Terrible Thing. However, did the object of his affection feel the same way? Did they date?

Matthew Perry was head over heels for one of his co-stars, did they date?

In his autobiography Friends, Lovers and the Big Terrible Thing, Matthew Perry admitted his deep feelings for one of his co-stars. This big-name star and the former Friends star had a short but sweet dalliance.

Perry wrote that he “fell madly in love” with co-star Valerie Bertinelli when they played siblings in the short-lived 1990 CBS sitcom Sydney. The series ran for one season on CBS from March through June 1990.

In the book, the actor claimed Bertinelli was “clearly in a troubled marriage” with her rock star husband, Eddie Van Halen. He revealed that he had “elaborate fantasies” about her leaving the rock star and them running away together.

“I was over at Valerie and Eddie’s house, just hanging out and gazing at Valerie, trying to make her laugh,” he wrote. “When you made her laugh, you felt 10 feet tall.”

He continued, “As the night progressed, it was clear that Eddie had enjoyed the fruits of the vine a little too hard, one more time, and eventually, he just passed out, not 10 feet away from us. But this was my chance!”

Perry added, “If you think I didn’t actually have a chance in hell, you’d be wrong, dear reader — Valerie and I had a long, elaborate make-out session. It was happening — maybe she felt the same way I did.”

“I told her I had thought about doing that for a long time, and she had said it right back to me,” Perry concluded.

However, their dalliance was reportedly only for that one short night. Shortly after that, Sydney was canceled, and the two went their separate ways.

Did Matthew Perry ever date any of his co-stars?

Matthew Perry’s romantic history includes a dalliance with one of his Friends co-stars. However, it wasn’t one of the core three women in the series.

No, Perry didn’t romance Jennifer Aniston, Courteney Cox, or Lisa Kudrow. Instead, he did briefly date Julia Roberts. The Oscar-winner appeared on the Friends Superbowl episode in 1996.

In his memoir, Perry revealed that he and Roberts dated in 1995, before she filmed her Friends installment titled “The One After the Superbowl.” It was more than just one or two dates, as Perry revealed he went to New Mexico to ring in 1996 with Roberts and her family.

“I did let her in, figuratively and literally, and a relationship began,” the actor wrote. “We would already be a couple by the time we started filming the Friends Super Bowl episode.”

However, it wasn’t Roberts who pulled the plug on the relationship. It was Perry.

“Two months later, I was single,” Perry wrote. “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, unloveable.”

Which celebrities did Matthew Perry date?

Matthew Perry was quite the man about town as a young actor. He dated quite a few celebrities.

He dated Tricia Fisher, sister of Star Wars actor Carrie Fisher when he was 18. He reportedly “made out” with Gwyneth Paltrow in 1994, the summer before Friends debuted on NBC.

Perry also dated Veep producer Gabrielle Allan, as well as Jamie Tarsas after her marriage to Fox TV producer Dan McDermott. Fashion student Rachel Dunn was next, followed by Natasha Wagner, the daughter of Natalie Wood and Richard Gregson.

He dated Cameron Diaz after her breakup with Justin Timberlake, leading to a six-year relationship with Mean Girls alum Lizzy Caplan.

Perry’s last relationship almost led to marriage. He proposed to literary manager Molly Hurwitz in 2020 after dating for two years. Six months later, the two called it quits in June 2021.

Matthew Perry died on Oct. 28, 2023, at his Los Angeles home. He was 54 years old.

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