36. Wilmer Valderrama and Lindsay Lohan

Another one of Wilmer Valderrama’s former lovers is none other than the 90’s to 2000’s teen queen herself: Lindsay Lohan. Valderrama and Lohan had chemistry and that we won’t deny, credits to their extreme good looks.Valderrama was Lohan’s first high profile boyfriend. With the level of fame they both had, they decided to announce their relationship publicly after the actress turned 18.

It was safer and less controversial that way as Valderrama was seven years older. Their relationship was described as not too deep but that didn’t stop Lohan from releasing her single Over after they broke up, which was about her heartbreak from Valderrama. Their relationship was over when Lohan had a series of unfortunate events in her life. She also admitted that she likes dating girls too. Valderrama, on the other hand, was labeled an official Hollywood playboy.