Length of Relationship: About a year
Just like everyone else, sometimes celebrity relationships don’t end well. Five years after their 2001 split, Wilmer Valderrama told Howard Stern that he took his then-teen girlfriend Mandy Moore's virginity.
"The sex with Mandy was good, but it wasn't like warm apple pie," he claimed. Moore clapped back in an interview with ELLE later that year, describing Valderama’s remark as "utterly tacky, not even true, and it hurt my feelings because I like him.”