29. Wilmer Valderrama
Wilmer and Lindsay actually dated for quite a while back in 2004. This was at the peak of Lohan’s career and Wilmer was a star on the popular series That ’70s Show. Hmm… wasn’t there another cast member of that show? Oh right, Ashton Kutcher.
Wilmer and Lindsay had to keep their relationship hush hush because at the beginning she wasn’t even 18 yet! Wilmer and Lindsay waited until her she was of legal age and then moved her into his house. Were they the OG Tyga and Kylie??
28. Ryan Phillippe
Ryan Phillippe and Lindsay were said to have hooked up back in ’07 when he was in the midst of his divorce with actress Reese Witherspoon. A year later, Phillippe appeared on The Howard Stern Show and admitted that Lindsay “wanted” him. The word is still out on whether Lindsay ever actually got what she “wanted”.
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