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Taylor Swift, Connor 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. They cuddled their way through Cape Cod – and even crashed a Kennedy family wedding. But those summer days and nights are over. On Thursday, as 24-year-old Swift prepares for her big performance at the MTV Video Music Awards in Hollywood, Conor heads back to high school. Yup, we said high school, not college. Conor, the eldest son of Robert F. Kennedy Jr. and the late Mary Kennedy, is due back at his posh boarding school, Deerfield Academy, in western Massachusetts on September 6, where he’ll begin 11th grade. And while his world-famous country singer girlfriend performs a track off her upcoming album, Red, at the VMAS on Thursday night, Conor will likely be catching her performance on a TV in his single-sex dorm room. Meanwhile, let’s hope Swift likes football because Connor, who plays at Deerfield, has games practically every weekend through early November. 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. Take a look at some of the (sometimes cringe-worthy) others...

Celebrities Who Dared to Date Teenagers

As Taylor Swift’s young boyfriend, Conor Kennedy, kicks off his junior year in high school, we look at other stars who have dared to date teenagers. -- By Suzy Byrne, omg! staff