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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.

I even tried it when my boyfriend and I took a short break, and I found it was painstakingly difficult and more complicated than my experience dating an older guy. The texting games (How long should I wait to text him back? It’s exhausting), the fear of commitment that plagues most twentysomethings, and the simple fact that most guys my age aren’t as emotionally mature as I am.

Miley Cyrus may be single at the moment, but the “Wrecking Ball” singer has had her fair share of suitors in the past.

Fresh off her breakup from Patrick Schwarzenegger, the former Disney Channel star revealed in 2015 that not all of her past relationships were “straight, heterosexual” ones. For me, I don’t want to label myself as anything,” she told magazine.

While you figure out the math, let me be clear that I’ve met several other women in their early- to mid-20s who also prefer to date from a much older pool for various reasons.

And while cliché dictates that, sure, men are into it, there’s been some recent research done about younger females often gravitate toward mature men.

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