Conquests of a Serial Dater: John Mayer’s Sex Life Revealed

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8) Taylor Swift

Everyone who loves to gossip loved the fact that John Mayer and Taylor Swift began to date in 2009 — not in the least because she was only 19 at the time. They both released songs about their relationship and its rocky road, including “Half of my Heart”, a collaborative effect. Swift’s post-breakup song “Dear John” was clearly aimed at him, with lyrics like “I was too young” and “You should’ve known”. Their relationship (or lack thereof) remains a sore spot for the two of them to this day, especially since they’ve both had mega-drama about boyfriends and girlfriends since.