Age difference: 4 years, 6 months, 19 days
Although she’s only 22, Swift has already been in (and written about) a lifetime of high-profile romances, including her time with John Mayer. But several of her boyfriends have been significantly younger than Swift. Taylor Lautner, her 2009 beau, was almost three years her junior, prompting one blog to ask: “Should a 17-Year-Old Date a 20-Year-Old?”. This summer, she started courting Kennedy scion Conor, when he was 17, according to several reports. “We’re told Conor’s cousins would accompany them on dates, but the family insisted they wait until after he turned 18 to come out as a couple,” reported Page Six. How serious is this love story? Now that Connor is 18, Swift has supposedly purchased a $4.9 million house in Hyannis Port, Mass., across the street from her new teenage man’s family property.