These Are The Famous Beautiful Women That Wilmer Valderrama Has Dated - Page 15 of 33

Ashlee Simpson – 2005

Simpson, the sister of singer and actress Jessica Simpson, was connected with Wilmer back in 2005. Even though it was never confirmed, Wilmer mentioned her when talking about his ex-girlfriends on “The Howard Stern Show.”

Supposedly Lindsay Lohan accused Simpson of stealing Valderrama from her, which inspired Simpson’s song “Boyfriend.” However, Simpson denied that Wilmer was the inspiration for the song.