The busty babe has a long list of hook-ups, but Wilmer was one of her most serious relationships. The actors dated for several months in 2004, when Linds was just 18 to his 24 years of age.

Lindsay soon grew bored of her steady relationship, however, and partied with a multitude of boys up until her current steady relationship, with girlfriend Samantha Ronson. 

And Wilmer is, well....maybe Tara Reid is available?