10. Taylor Swift – Jake Gyllenhaal
Some believed that John Mayer was the culprit behind Taylor Swift’s lost virginity. However, it would be the Love And Other Drugs star that would deflower the pop princess. While they dated back in 2010, it was at Swift’s 21stbirthday party that everything blew up. She had been dating Gyllenhaal and despite stating that she was saving herself for marriage, Swift had the realization that she and Gyllenhaal were destined for wedding bells. Didn’t happen and Gyllenhaal stood Swift up at her 21st birthday and that was that. They had a bad relationship and no doubt there are numerous Swift songs dedicated to the break-up.
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