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Conor Kennedy, Taylor Swift's Boyfriend, Unlikely To Get Permission To Attend VMAs

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This Thursday, Taylor Swift will be performing her new hit song, "We Are Never Getting Back Together," at the MTV Video Music Awards in Los Angeles. Also on Thursday, her boyfriend, Conor Kennedy, should be attending his first day of school at Deerfield Academy in Massachusetts. Insiders are left to ask, will Conor dare skip school to be with his girlfriend?

“If Taylor can send a plane to bring him to Nashville after she had to leave his side for just one week then anything is possible,” one former MTV executive told me. “Everyone is hoping that Taylor and Conor attend together. It would be great buzz for the show to have these two walk their first red carpet together.”

Juniors at Deerfield are scheduled to start the new school year on Thursday with a mandatory 9:30 a.m. arrival time, and night visiting hours end at 9:45 p.m. sharp. This would make it impossible for Conor to be with Taylor in California, even if Taylor did pay for a private plane.

“With one year left to graduation, he will not be allowed a ‘special pass’ to let him attend the VMAs," an expert on higher education tells me. "If he was ill or had a family crisis, an exception would be made. But no way would the school agree that seeing his famous girlfriend perform would be more important than his education. What sort of message would that send to other students or about how seriously the school takes its work?"

It should also be noted that Thursday isn’t just a major day for Taylor Swift and her 18-year-old boyfriend. President Barack Obama accepts his party’s nomination in Charlotte, N.C., on Thursday as well.

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