Jared Leto, 1992
In 1992, the teen drama series “My So-Called Life” starred Jared Leto playing the dreamy Jordan Catalano. Leto appeared alongside the then-14-year-old Clare Danes. He ended up being the actress’s first kiss, where she described the encounter as “ridiculous.”
Glenn Close and Woody Harrelson
Glenn Close, who played Cruella De Vil in the film 101 Dalmatians, had a relationship with Woody Harrelson in 1991. Close was 14 years older than the Cheers star Harrelson. While the relationship between the two did not last, they remained good friends to this day.