Clearly happy to go their separate ways, Linda’s next move in the romance department was an interesting one.Then 49, she started seeing a 19-year-old who had attended high school with her daughter, Brooke, and son, Nick.That's all I really want to say about it." In 2001, Aaliyah died in a plane crash when she was just 22.In the years following her death, Kelly was involved in a legal drama over a video which reportedly showed him having sex with his then-underage goddaughter.In November, just weeks after Lohan made a cameo appearance on Valderrama's TV series, they called it quits.Lohan's mom, Dina, later called Valderrama her daughter's "first love."Wilmer Valderrama and Mandy Moore Valderrama had previous experience with younger ladies.
"I'm totally freaked out," Brooke said at the time.
In 2009, she announced their split on Twitter, writing, "Why does saying good-bye hurt so much? “We want to have a long engagement," Miley recently told Marie Claire.
Jerry Seinfeld and Shoshanna Lonstein Jerry Seinfeld was at the peak of his success while starring in his iconic TV series, “Seinfeld,” and had his pick of ladies – not that there was anything wrong with that.
Although he was initially charged with child pornography, the "Feelin' on Yo Booty" singer was later acquitted.
Linda Hogan and this 19 year old After 24 years of marriage, Linda and Hulk Hogan’s 2007 divorce was a nasty one with accusations aplenty.
But Swift isn’t the only mega-star who has pursued a relationship with someone who was still treading through his or her teen years.