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Friends fans already miss Matthew Perry. The Chandler Bing actor died in October 2023, and he wasn’t married at the time of his death. While he once spoke about potentially marrying his most recent ex-fiancée, Molly Hurwitz, their relationship didn’t work out. And Hurwitz allegedly lost “romantic” interest in Perry following a scandal with the dating app Raya.

Matthew Perry’s ex-fiancée, Molly Hurwitz, allegedly lost interest in Perry

Matthew Perry thought he found “the one” with Molly Hurwitz. The Friends actor started dating the literary agent in 2018, and they were engaged by November 2020. Perry was 22 years older than Hurwitz.

“I decided to get engaged,” Perry told People in 2020. “Luckily, I happened to be dating the greatest woman on the face of the planet at this time.”

Another source shared with OK! Magazine that Perry was happy and motivated with Hurwitz by his side. “Matthew’s been to hell and back. He feels extremely proud to have turned his life around from rock bottom,” the insider shared. “He’s never been so content. … He knew he had to get healthier if he wanted to live long and prosper, and Molly’s love definitely spurred him to action.”

By 2021, Perry called off his engagement to Hurwitz. “Sometimes, things just don’t work out, and this is one of them,” he told the publication. “I wish Molly the best.”

So, what happened? Perry didn’t elaborate to People about why he and Hurwitz went their separate ways. But sources alleged to OK! Magazine that Hurwitz was “losing interest in Matthew romantically, and he could pick up on it.”

“Molly is telling people this is not a pause,” another source noted. “It’s over.”

'Friends' stars Matthew Perry, Jennifer Aniston, David Schwimmer, Courteney Cox, Matt Le Blanc, and Lisa Kudrow posing with milkshakes
The cast of ‘Friends’ | NBCU Photo Bank/NBCUniversal via Getty Images via Getty Images
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The ‘Friends’ star allegedly messaged a much younger woman on Raya during a break from Molly Hurwitz

Additional rumors suggested Matthew Perry and Molly Hurwitz experienced strain in their relationship after he allegedly messaged a much younger woman on the dating app Raya. Perry and Hurwitz were taking a break from their relationship at the time that the alleged exchange took place. OK! Magazine reports Hurwitz felt “unsettled” by Perry’s activity on Raya before they officially called off their engagement.

The woman Perry matched with, Kate Haralson, was 19 years old. She posted about the exchange to TikTok and claimed that Perry tried to FaceTime her quickly after matching. “When you match with Matthew Perry as a joke on a dating app and he FaceTimes you and plays 20 questions with you,” she wrote in the clip.

“A lot of people were saying I’m a bully and mean for posting this, and it made me feel kind of bad, but at the same time, I feel like a lot of guys in Hollywood are talking to all these young girls and it’s something that I think a lot of people should be aware of,” Haralson told Page Six.

Matthew Perry worried that women only dated him for his money

Sources told the Daily Mail that Matthew Perry had difficulty dating because he feared that women only wanted him for his money.

“Matthew dated dozens of women. But in the end, he always felt they were only interested in his money and his fame,” the source shared. “And he was generous to a fault. He would shower women with gifts only to have them pack up their goodies and walk away. In the end, I think his years of fighting demons … drugs and alcohol … took a toll on him, and on his health, and eventually, he would end up alone again.”

“All Matt ever wanted was to be happy,” the source continued. “But he was always looking for love and happiness in all the wrong places.”

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