Pacific Palisades, California - Could this be any more upsetting? Friends star Matthew Perry and his fiancée Molly Hurwitz have unfortunately ended their engagement.

The actor proposed to the literary agent in November 2020 after about a year of dating.

Neither Perry nor Hurwitz have gone into depth as to what caused the heartbreaking split.

However, on Tuesday, the Fools Rush In star confirmed to People that he ended the relationship.

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"Sometimes things just don't work out and this is one of them. I wish Molly the best," Perry explained to the outlet.

Before his romance with Hurwitz, Perry was involved with Now You Can See Me star Lizzy Caplan from 2012 to 2016.

His most high-profile relationship was in the 90s, when he dated Julia Roberts for a year.

The unhappy news follows Perry's recent emotional reunion with his five former Friends castmates for their hit sitcom's highly-anticipated HBO Max special.

The star, who played Chandler Bing, joined Jennifer Aniston, David Schwimmer, Courteney Cox, Matt LeBlanc, and Lisa Kudrow on Stage 24 – where the show was originally shot – for the first time in nearly 20 years.

In addition to his love life, Perry has dealt with personal struggles throughout his career.

The actor battled an addiction to Vicodin which drastically affected his health.

During the reunion special, the star also shared that he dealt with anxiety during his time on Friends, even though his character was responsible for delivering some of the most memorable jokes on the show.

Now, Matthew Perry is a single man again, and things are looking up: The actor will appear on Netflix in the upcoming comedy, Don't Look Up, later this year.