Johnny Depp and Winona Ryder
Credit: Johnny & Winona
In 1990, Depp and Ryder met at a movie premiere and dated for five months before getting engaged. Depp told People at the time, “There’s been nothing in my 27 years that’s comparable to the feeling I have with Winona.” He even got a “Winona Forever” tattoo on his arm, but apparently “forever” means 3 years because that’s when the relationship ended. Depp changed the tattoo to “Wino Forever.” Depp went on to have two children with French singer Vanessa Paradis. Later he married actress Amber Heard but their volatile marriage ended after two years.