Jennifer Grey Relationship History: See Who the ‘Dirty Dancing’ Star Has Dated Over the Years!
Plus, you won't believe the two Hollywood stars she was engaged to within the same month!
Not many people can say they were engaged to two of the biggest actors in Hollywood within the same month—but Jennifer Grey can! The big-screen starlet of the 80s, known for her work in iconic films like Dirty Dancing (1987), Red Dawn (1984) and Ferris Bueller’s Day Off (1986), is known for her impressive resume, but she also made headlines throughout her youth for her romantic relationships as well! From A-List actors to political figures, take a look at the whirlwind romances of Jennifer Grey.
Jennifer Grey and Michael J. Fox, mid-’80s
One of the actress’s earliest rumored relationships is said to be with fellow film icon Michael J. Fox around the mid-80s. At the time, the duo were both cementing their status as Hollywood stars, with Fox starring in 1985’s Back to the Future and the hit sitcom Family Ties and Grey making her presence known in a few big films of the time as well. Despite things ending between them, back in 2023, Fox referred to the actress as “My friend Jennifer Grey,” when referring to her memoir in an interview with Variety.
Jennifer Grey and Matthew Broderick, 1985—1988
Jennifer Grey and Matthew Broderick first linked up on the set of Ferris Bueller’s Day Off, and what started as a romance between co-stars evolved into something much more serious. In 1988, he popped the question, but their relationship wasn’t without strife. In 1987, mere weeks before the release of Dirty Dancing, Grey and Broderick were involved in a fatal car crash in Ireland in which Broderick was behind the wheel. Two women were killed in the crash, and it’s something the actress has spoken about publicly.
“I was the sole living witness, because Matthew had survived, but he was unconscious and had amnesia and was very badly injured. I thought he was dead,” she told Entertainment Tonight in 2022. “I didn’t even know there were two other women who were tragically killed at the time. It’s just something that you just don’t come back from in the same way.” In 1988, Grey and Broderick went their separate ways.
Jennifer Grey and Johnny Depp, circa 1988
Not long after splitting with Broderick, Grey went on a blind date with none other than Johnny Depp—and within a few weeks, Depp had proposed to the actress. Grey revealed on The Drew Barrymore Show that she was engaged to both Depp and Broderick within the same month! “It was really a sign that there was trouble afoot on my part,” she joked with Barrymore. “I just thought it was God rescuing me from one bad situation and just lovingly plopping me into a Johnny Depp souffle.”
Jennifer Grey and William Baldwin, late ‘80s, early ‘90s
Grey dated Alec Baldwin’s brother William, and it was none other than Madonna who set her up with him! Ironically, Grey had a crush on Alec Baldwin at the time, and when Madonna invited him to the birthday party she was throwing for Grey, he brought his brother along. Taken by William, the two ended up dating for a bit after!
Jennifer Grey and George Stephanopoulos, early ‘90s
Grey was reportedly tied to former Communications Director and eventual advisor for President Bill Clinton back in the early ’90s, but things eventually fizzled out.
Jennifer Grey and Clark Gregg
Grey’s most serious partnership was with Clark Gregg, whom she was married to for 19 years before calling it quits in 2020. Together, they share a daughter, Stella.
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