In 2000, Mandy Moore was a fresh-faced 16-year-old who had recently landed a Neutrogena contract and her own show on MTV.
She met Valderrama, then 20, soon after at a photo shoot and they started dating.
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.
"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.
Lonstein, now a fashion designer, later told Details, “I felt like I was losing myself” by dating Seinfeld, who she called a workaholic. They met weeks after Jessica had married someone else.
She then quickly filed for divorce and started dating the famed comedian.