The Many Boyfriends of Taylor Swift

Photo: Wikimedia Commons

2008: Joe Jonas

It’s not clear whether she simply rolled a Jonas die and it landed on Joe, or she sat down with pictures of each brother and analyzed them. What is certain, however, is that Taylor and Joe were hot and heavy back when the two were wee 18-year-olds. What’s even cuter: they went to each others’ concerts. All good things must come to (a quick) end though, as Jonas dumped Swift via 27-second phone call (who among us hasn’t used that maneuver?)

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2009: Taylor Lautner

Back in 2009, Swift was the #1 member of “Team Jacob.” The pair went on many adorable fro-yo dates. Alas though, Lautner was more into the darling starlet than she was to him, and the courtship was cut short. You could say Swift sucked the blood out of Lautner.

Photo: Wikimedia Commons

2009-2010: John Mayer

At this point, it seems as if Swift sat down and decided that if she was going to date celebrities, she was going to shoot for the sky. Her plan worked, as it scored her inveterate ladies’ man John Mayer, he of Jessica Simpson and Jennifer Aniston fame. Oh, but how things got nasty, and you know how it is with songwriters—the relationship’s tumultuous end slinked its way into Swift’s “Dear John.”

Photo: Wikimedia Commons

2010-2011: Jake Gyllenhaal

Jake Gyllenhaal- Swift and Gyllenhaal got together when Swift was 21 and Gyllenhaal was 30. Age proved to be but a number as the couple was spotted dining and carousing backstage during SNL. The relationship was short-lived, however, as Gyllenhaal became displeased with the heaps of publicity the couple received.

Photo: Facebook/Conor Kennedy

2012-Present: Conor Kennedy

Swift’s switched her style up with her acquisition of love mate Conor Kennedy. Almost ten years her senior? Nope (he’s four years younger). A major Hollywood celebrity? Na na. The relatively obscure scion of a revered American family? You betcha. Swift and Kennedy enjoyed quite the summer fling in the far reaches of New England snobbery, i.e. Hyannisport. And they’re still going strong to this day, with recent reports that Swift kidnapped the delightfully disheveled-looking Kennedy.