Matthew Perry Just Ended His Engagement. Here's Why

Matthew Perry has headed to splitsville again after calling it quits with his fiancée, Molly Hurwitz. The "Friends" star has quite the dating history, which includes big name stars including Julia Roberts, Yasmine Bleeth, and Heather Graham (via The Sun) and he also enjoyed a lengthy romance with "Mean Girls" actor Lizzy Caplan from 2006 until 2012.

Perry and Caplan quietly split, with a source alleging to Daily Mail that things ended because Perry supposedly "wasn't ready to make the full commitment." He appeared to take a break from dating in the public eye after that and told USA Today in 2013 that he was dating "a little bit" but had decided to keep that part of his life a little more private.

It seemed like he'd finally found that special someone when he started dating Hurwitz in 2018. However, In Touch reported that Perry and Hurwitz split in May 2020, with a source claiming the breakup "was very amicable, but they have both decided to go their separate ways." Perry confirmed in November 2020 that things were very much back on and serious when he told People that he'd popped the question. "Luckily, I happened to be dating the greatest woman on the face of the planet at this time," he gushed. Sadly, fast-forward seven months and it was all off once again.

So, what really happened between Perry and Hurwitz this time? Keep scrolling for the details.

Matthew Perry's split with Molly Hurwitz had some interesting timing

Matthew Perry confirmed on June 1 that he had called off his engagement to Molly Hurwitz. As for what went wrong, the "Friends" star explained in a statement issued to People, "Sometimes things just don't work out and this is one of them." So, where does the now former couple's relationship stand in the wake of their split? It seems like things are amicable, as Perry added, "I wish Molly the best."

The two don't appear to have offered any further explanation about what led to their apparent second breakup just yet, though the news came just days after Perry was thrust firmly back in the spotlight for reuniting with his "Friends" co-stars, Courteney Cox, Matt LeBlanc, Jennifer Aniston, Lisa Kudrow, and David Schwimmer. The cast were on everyone's lips as they got back together to reflect on the phenomenon and Perry in particular had people talking after the special hit streaming services on May 27.

Just a few days before "Friends: The Reunion" aired, Perry also hit the headlines for an alleged interaction on the dating app Raya. A 19-year-old woman claimed to have matched with the actor on the app in May 2020 and dished on their supposed exchange to Page Six. It's not clear how much, if any, impact that had on his split with Hurwitz. 

Whatever happens between Matthew Perry and Molly Hurwitz in the future, we're wishing them both the best.