Taylor Swift certainly does play the field. She's dated a lot of guys, however briefly and innocently, in her teens and 20s. Here's a look back!

Jake Gyllenhaal
Jake Gyllenhaal allegedly took Taylor Swift's v-card, then dumped her via text. TEXT.
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at least 5 of these guys have never went out with Taylor, thats so stupid

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Who gives a rat's @$$ about Taylor Swift? She is the definition of an overrated pop singer. She's parlayed breakups into a cottage industry. She is sooo phony, almost a caricature.