At the peak of his fame, Matthew Perry dated some of Hollywood’s most famous women.
But one relationship has always haunted the actor.actor had relationships with the likes of Julia Roberts, Cameron Diaz, Gwyneth Paltrowand Yasmine Bleeth, who was also the on-screen crush of his character Chandler Bing.But the star never married or had children, saying it was his failure to propose to actress Lizzy Caplan which always ‘haunted’ him.magazine in October 2022, the actor cited his insecurities for one of the reasons why he never truly settled down.
“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.”actor said his feeling ran deep feelings for Bertinelli, it was clear she regretted the kiss as the next day she “made no mention” of what transpired and behaved “as she should have”.
“At some big party we slipped off into a broom cupboard and made out,” he wrote. “We were both still unknown enough that it didn’t make it to the tabloids.”, “Hopefully, she’ll find it to be a cute story. It’d be bad if Gwyneth Paltrow hated me; I wouldn’t like that.”“I met Matthew Perry in 1993 at the Williamstown Theater Festival in Massachusetts. We were both there for most of the summer doing plays,” she shared on Instagram alongside a photo of Perry.
The pair then embarked on a three-month relationship but Perry ultimately ended it as he felt inadequate to be dating a major movie star – he felt like she was “slumming it with a TV guy”. “There was no drama involved , just a commitment by Matthew to stay focused on his sobriety,” a source told the outlet.Perry was set up on a date with Cameron Diaz shortly after her split with Justin Timberlake in 2007 following a four-year relationship.
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