Matthew Perry and Molly Hurwitz have been through some high and lows since they first struck up a romance.
The Friends actor, 51, recently proposed to the talent manager, 29, after two years of dating. But the relationship hasn’t always been smooth sailing.
Here’s a look back at Perry and Hurwitz’s relationship.
2018: Perry and Hurwitz start dating sometime in 2018.
According to The Sun, Perry and Hurwitz mixed “in the same circles”, and hit it off immediately.
“She’s originally from New York where they have spent time together,” a source tells the publication, explaining Perry liked her “very quirky sense of humour”.
November 2019: Their relationship remains mostly private until the couple are seen on a date at a swanky Los Angeles restaurant.
“[Hurwitz is] telling friends that she is not in it for fame, but she secretly loves the attention she’s been getting from their relationship,” a source tells Us Weekly at the time. “The guys she has dated in the past have all been in the entertainment industry.”
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February 2020: Hurwitz confirms the relationship by sharing a sweet message for the actor on Valentine’s Day.
“Second year being my valentine, but his first as an Instagram influencer,” she writes on her private Instagram account — which she later deletes. “HVD to my favourite.” Perry had recently joined the platform at the time.
May 2020: The couple split up.
“It was very amicable, but they have both decided to go their separate ways,” an insider tells In Touch Weekly.
Following their breakup, Perry is spotted on the celebrity dating app Raya.
The couple later reunite.
READ MORE: Who is Matthew Perry’s new fiancée, Molly Hurwitz?
November 2020: Perry and Hurwitz become engaged!
On November 26, the actor announces that he popped the question to his girlfriend.
“I decided to get engaged,” Perry tells People. “Luckily, I happened to be dating the greatest woman on the face of the planet at this time.”
December 2020: Perry shares the first photo of his fiancée on his Instagram account.
In the photo, Hurwitz is wearing a shirt that reads, “Could this BE any more of a T-shirt?” referencing Perry’s character, Chandler Bing, and his famous catchphrase from Friends.
June 2021: On June 1, the day before Hurwitz’s 30th birthday, Perry tells People the engagement is off.
“Sometimes things just don’t work out and this is one of them,” Perry says in an official statement. “I wish Molly the best.”