4. KRISTEN ZANG

When: Early 1992 - Mid 1994
Ever the heartbreaker, a 29-year-old Nicolas Cage proposed to his then 19-year-old aspiring actress girlfriend with a grand gesture in Central Park, only to dump her soon after via telephone for the more established actress, Patricia Arquette.

Smash Probability: Cage was obviously re-living his 1980s teen romcoms by dating her.