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They may not quite be friends any more, but Taylor and Katy have both dated John Mayer. Katy and John began their romance in 2012 and famously dated on and off for almost two years; they broke up in February 2014 but are rumored to have reconnected. Taylor was linked to John back in 2009, although it's not clear how long their relationship lasted — though we do have her song "Dear John" and his tune "Paper Doll" to help put the pieces together.