3. Johnny Depp & Winona Ryder Years Together: Began dating in 1989, engaged from 1990 to 1993. Why They Split: It seems as though Johnny had places to be and models to date. Why They're Better Off Together: The world's first indie couple, they made a romance between a regular girl and weapon-handed boy believable. And Johnny just can't have that dumb "Wino Forever" tattoo, well, forever.