Taylor Swift

Despite being only 27, Taylor is swiftly making her way to the top of the “Most Exes” list, many of which are Hollywood A-listers. She has dated somewhere around a dozen different famous stars, including Jake Gyllenhaal, John Mayer, Harry Styles, and Calvin Harris, with none of these flames lasting longer than a year. As we all know, her trademark is writing a hit song or two about the breakup in not-so-subtle lyrics, which is a fan’s best insight into what made her latest relationship crash and burn. T-Swift’s long list of boyfriends past might make her unlucky in love, but her bank account is just the opposite! Word on the street is that she’s back on the market…looks like she’s got another blank space–in her wallet!