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Conor Kennedy

House-hunting and wedding crashing were just a few of the activities Taylor Swift, 22, indulged in while dating Conor Kennedy, 18-year-old son of Robert Kennedy Jr. The couple dated for three months and called off their summer romance by October 2012. Earlier that summer, Swift had been spotted with Maria Shriver's son Patrick Schwarzenegger, another Kennedy descendant, on the Fourth of July. Jason Kempin / Getty Images