10. Lindsay Lohan & Wilmer Valderamma
Back when Lindsay‘s future looked brighter than it actually turned out to be, the 17 year old Mean Girls star dated Wilmer Valderamma, in 2004. Though the pair were often photographed together, they decided against going public until Lindsay turned 18 that summer. The That 70’s Show star toldPeople Magazine the same year, “We try to keep it more under wraps because it is a lot more meaningful that way. At this point we don’t need all the free press.” By meaningful, we’re sure he meant to say against the law. The pair ended up parting ways just the following year. Undisturbed by the age gap, Dina Lohan would later refer to Wilmer as her daughter’s “first love”. In 2014, Lindsay shared with Ellen Degeneres that the single Over, from her long forgotten debut album Speak, was about her break up with Wilmer.
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