Photo: Kevin Mazur/WireImage/Jim Spellman/WireImage
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Only time will tell if Katy is destined to be more than another name on John's starry list of romantic conquests, which includes Jennifer Aniston, Jessica Simpson, Jennifer Love Hewitt, and Minka Kelly. But his most recent high-profile flame pre-Katy was a then barely legal Taylor Swift, who he romanced back in 2009. Whether or not Katy is an upgrade, at least we can agree John is dating someone more age appropriate now!