Matthew Perry has recently found himself single again.
The 51-year-old actor and Molly Hurwitz announced the end of their engagement in June 2021.
“There was a lot of flirting over faxing.

She was giving him these questionnaires like, ‘Why should I go out with you?’
And everyone in the writers room helped him explain to her why.”
“They were just dinner and nothing happened,” Perry said of the meet-ups toEntertainment Weekly.

“I was confused about dating before ‘Friends’.
This all just makes it more confusing.”
Still, the couple didn’t last long, splitting up after just a few months together.

Perry was linked to a number of famous faces throughout the remainder of 1996.
Later that year, Perry checked himself into rehab for struggles with prescription pills.
If you or anyone you know is struggling with addiction issues, help is available.

Visit theSubstance Abuse and Mental Health Services Administration websiteor contact SAMHSA’s National Helpline at 1-800-662-HELP (4357).
When he met co-star Neve Campbell, sparks flew.
It didn’t last, however, and the two were broken up before the film’s release.

After the relationship, Perry worked on keeping his relationships out of the public eye.
From the end of their relationship in 1998 until 2002, Perry didn’t publicly cop to dating anyone.
In 2002, the actor began dating “Bold & The Beautiful” star Maeve Quinlan.

Perry followed the relationship with a brief fling with Heather Graham.
The two reportedly put their chemistry to the test in 2003 and briefly dated (perIn Touch Weekly).
Things didn’t work out between them but they continued to be friends and work together again.
Later in 2003, Perry met Rachel Dunn, a fashion student 14 years younger than him.
The two hit it off and proceeded to date for two years.
In the end, their lives were in different places.
From 2006 to 2012, the two didn’t formally discuss their relationship in interviews.
Caplan did seem to allude to her relationship with Perry in an interview with The Independent discussing paparazzi.
The public wouldn’t find out the two split for over a year after the breakup.
Sources indicated that the split came because Caplan was ready to settle down, but Perry had concerns.
In 2018, the actor met talent manager Molly Hurwitz and the two began seeing each other.
On Valentine’s Day 2020, Hurwitz made it official with an Instagram photo of the two of them.
They would briefly split mid-year, only to reconcile within weeks.
Later that year around Thanksgiving, Perry would reveal the two got engaged.
“I decided to get engaged,” he toldPeople.
It seemed like Perry had finally met his match, but sadly the relationship didn’t work out.
In early June 2021, Perry announced the two had broken up, wishing Hurwitz the best.