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Slide 5 of 49

Johnny Depp and Winona Ryder

Johnny hooked up with his Edward Scissorhands costar Winona Ryder in the late '80s. Things got serious fast, and the two got engaged in 1990. Johnny got inked with his infamous "Winona Forever" tattoo, which he tweaked to read "Wino Forever" after they broke up in 1993. Winona has since called the split her "first heartbreak."

Image Source: Getty / Kevin Mazur