#9: Jennifer Grey (1988-1989)
Jennifer Grey, best known for Dirty Dancing, had a brief chapter with Johnny Depp in the late ’80s. They were engaged for a hot second—famous, young, attractive—and then, just as quickly, it was over. Neither has ever shared much about the breakup, and perhaps that’s the most telling part: not all celebrity romances demand tabloid autopsies.

Their relationship was like a flashbulb—bright, fast, and gone. It wasn’t messy. It didn’t define either of them. But it added another page to Depp’s pre-superstardom romantic history, a reminder that even in the early days, he moved fast through connection and change.
