A Complete Ranking of Taylor Swift’s Confirmed & Rumored Ex-Boyfriends

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16. Sam Armstrong


This boyfriend is from the pre-celebrity days (duh — look at the quality of that pic!), and he's also one who cheated on our girl. While he inspired an early Taylor anthem, “Should've Said No,” which we're grateful for, it's pretty gross that he had to cheat on her to do so. Completely unacceptable. For not appreciating having a goddess by his side, he takes the spot as her worst boyfriend and he totally deserves it.