Matthew Perry dated some of the most beautiful women in Hollywood

The world mourned the loss of Matthew Perry, the beloved actor from 'Friends', who tragically passed away at the young age of 54 on Saturday, October 28. Although he never had the opportunity to say "I do," Perry was once engaged to a literary manager and had affairs with some of the most beautiful women in Hollywood at the height of his 'Friends' fame. But his final days saw him embrace singlehood, at least publicly, as he focussed on his sobriety. As we fondly remember his life, lets embark on a journey through the pages of his romantic life.

Julia Roberts

In the mid-'90s, Perry was linked to Hollywood royalty, Julia Roberts. Their brief yet high-profile relationship stirred up quite the buzz in the entertainment world. As Perry wrote in his memoir 'Friends, Lovers and the Big Terrible Thing', he was “walking on air” while dating Roberts.

Yasmine Bleeth

Perry's dating history continued to make headlines as he reportedly dated 'Baywatch' beauty Yasmine Bleeth. Their romance was short-lived, but it was enough to keep fans taking as Perry's Chandler Bing on 'Friends' also had a thing for the 'Baywatch' beauty.

Lizzy Caplan

Perry's most notable long-term relationship was with 'Mean Girls' actress Lizzy Caplan. The couple dated for several years and appeared together at various red carpet events, making them one of Hollywood's most-watched couples.

Lauren Graham

Perry and Lauren Graham, famous for her role in 'Gilmore Girls', were rumored to be an item in the early 2000s. Though their relationship was never officially confirmed, Graham mentioned Perry in her 2016 memoir, 'Talking As Fast As I Can' penning, “He became my longtime Friend Who I Almost But Never Exactly Dated, or FWIABNED.”

Molly Hurwitz

Perry's most recent and widely publicized relationship was with literary manager Molly Hurwitz. The couple got engaged in 2020 after they began dating in 2018, and their love story was a testament to Perry's journey towards happiness. Unfortunately, the pair split in 2021 with Perry stating, “Sometimes things just don’t work out and this is one of them, I wish Molly the best.”

Gwyneth Paltrow

After Perry's passing, Gwyneth Paltrow took to Instagram to pay her respects to the actor. In her post, she revealed that she and Perry had a brief summer fling, just before 'Friends' propelled him to megastardom. “We drove out to swim in creeks, had beers in the local college bar, kissed in a field of long grass. It was a magical summer,” Paltrow’s captioned the post.