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Lohan's mom, Dina, later called Valderrama her daughter's "first love."Wilmer Valderrama and Mandy Moore Valderrama had previous experience with younger ladies.
They met through Miley’s dad – Billy Ray hosted “Nashville Star,” the reality show on which Gaston was a contestant. We will smile again." Well, she certainly smiled when new love Hemsworth, 22, popped the question in May 2012.Talk about being in different places in their lives!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.They cuddled their way through Cape Cod – and even crashed a Kennedy family wedding. On Thursday, as 22-year-old Swift was preparing for her big performance at the MTV Video Music Awards in Hollywood, Conor headed back to high school. Meanwhile, let’s hope Swift likes football because Connor, who plays at Deerfield, has games practically every weekend through early November. and the late Mary Kennedy, was due back at his posh boarding school, Deerfield Academy, in western Massachusetts on September 6.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.
However, the one who caught his eye in Central Park in 1993 was Shoshanna Lonstein – who was just 17 and a senior at the private Nightingale-Bamford School in Manhattan.In 2006, he appeared on Howard Stern’s radio show and talked about how he took Moore’s virginity.She later told Elle that his comments were "utterly tacky, not even true, and it hurt my feelings because I like him."Aaliyah and R Kelly Looking back, it was no surprise Aaliyah’s 1994 debut album was called Age Ain’t Nothing but a Number.When Vibe produced a copy of the marriage license in 1995, she responded, "I'm not married.That's all I really want to say about it." In 2001, Aaliyah died in a plane crash when she was just 22.Despite their daughter’s young age, Miley’s parents were both happy about the relationship with Billy Ray calling it “a good thing." No surprise, what Miley and Gaston had wasn’t an everlasting love. However, “The Last Song” co-stars aren’t rushing down the aisle.