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.Miley Cyrus and Justin Gaston Before Liam Hemsworth was ever a thought in her mind, Miley Cyrus was head-over-heels for another older guy named … In 2008, when the “Hannah Montana” star was only 15, she started dating the 20-year-old model.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.
Then 17, Lohan, who had already begun to earn her party girl reputation, started hanging out with “That ‘70s Show” star Wilmer Valderrama. “We try to keep it more under wraps because it is a lot more meaningful that way," Valderrama said that summer, adding: "We don't need the free press." Once they went public, things didn’t last long.
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.
Taylor Swift and Conor Kennedy Taylor Swift enjoyed some summer lovin’ over the last few months, proceeding at full throttle into a relationship with 18-year-old Conor Kennedy. And while his world-famous country singer girlfriend performed a track off her upcoming album, Red, at the VMAs on Thursday night, Conor most likely had to catch her performance on a TV in his single-sex dorm room.
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.
Although their relationship ended in 2002, Valderrama apparently couldn’t keep Moore off his mind.