Monday, June 1, 2026

Taylor Swift Has VMAs on Thursday, Conor Kennedy Has High School

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On Thursday a lot happens: while President Barack Obama makes a very important acceptance speech in Charlotte, North Carolina, Madonna will be playing at Yankee Stadium. Fashion Week will start in New York and Los Angeles with boutique-crawls. And the Toronto Film Festival opens with Rian Johnson’s “Looper.”

But more earth-shaking: while Taylor Swift performs at the MTV Video Music Awards in Hollywood, her 18 year old boyfriend Conor Kennedy is supposed to be at the first day for returning students at Deerfield Academy in western Massachusetts.

Kennedy is starting his junior year at Deerfield, a school famous its alumni including writer John Gunter, whose classic memoir “Death Be Not Proud” is set at the school. Returning students are mandated to be at school at 9:30am on the 6th, with a full day of classes on Friday.

It’s doubtful that with two years left til graduation Kennedy will be allowed an excuse to attend the VMAs at the Staples Center. Instead he will have to watch Swift, 22, sing “I Will Never Ever Date a Celebrity and Write a Song About It” from his dorm room. Taylor will sing the song with fingers crossed behind her back.Conor will no doubt be razzed by his buddies, who may not seen him since tragic death of his mother, Mary Richardson Kennedy, last May.

Recently, there were reports that Taylor sent a plane for Conor because she missed him so much wherever she was–Nashville, probably. But it’s unlikely that plane will be landing at Deerfield on Thursday morning.

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Roger Friedman
Roger Friedmanhttps://www.showbiz411.com
Roger Friedman is the founder and editor-in-chief of Showbiz411. He wrote the FOX411 column on FoxNews.com from 1999 to 2009 and previously edited Fame magazine and wrote the "Intelligencer" column at New York magazine. His bylines have appeared in The New York Times, The Washington Post, the New York Daily News, the New York Post, Vogue, Details, and the Miami Herald. He is a voting member of the Critics Choice Awards (Film and Television branches), and his movie reviews are tracked by Rotten Tomatoes. is articles have appeared in dozens of publications over the years including New York Magazine, where he wrote the Intelligencer column in the mid 90s and covered the OJ Simpson trial, and Fox News (when it wasn't so crazy) where he covered Michael Jackson. With D.A. Pennebaker and Chris Hegedus, he co-produced the 2002 documentary "Only the Strong Survive," which screened at Directors' Fortnight at the Cannes Film Festival.

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