Mandy Moore – 2000-2002

Wilmer dated actress Mandy Moore from 2000-2002, back when she was 15 years old and working on teen movies such as “The Princess Diaries.” She had just ventured into big-time acting after making a name for herself from singing.

In 2006, years after they broke up, Valderrama talked to Howard Stern on his show and mentioned his intimate relationship with Mandy. He also claimed that he was her first, which she denied. Moore also recently spoke with Stern and claimed what Valderrama said was false. The two remained friends, but she was shocked to hear he made those remarks about their time together.