44. Lindsay Lohan and Wilmer Valderrama
Couple Nickname: None
Dated Between: 2004
Another relationship from Lindsay Lohan's more innocent times that earns a spot on this list is undoubtedly the four-month-long one she shared with former That 70's Show star Wilmer Valderamma.
Their relationship, in reality, probably lasted a lot longer. Reports of them dating weren't confirmed until Lilo's 18th birthday seeing as Valderrama was 24 at the time, but the two had been spotted together for months before. Not much to say about the actual relationship as it was so short, but the few months Valderrama was basically dating an underage girl? Not cool.