King of the Fling: The late-night exploits of Derek Jeter

Some people truly have it all, and Yankees legend Derek Jeter is one of those people. Now he’s a married man. But in his heyday, Jeter was not just the face of the most prestigious franchise in baseball, he was also quite the ladies man. Jeter was known to have one-night stands with women and send them home the next morning with a gift basket of memorabilia, a ritual that may walk the line between classy and sleazy but is also 100% brilliant.

Of course, when he wasn’t obsessed with carrying one-night flings with random but undoubtedly gorgeous women, Jeter was wining and dining an almost endless parade of beautiful women who may have actually had more than one date with the future Hall of Famer in what amounts to an absolutely epic dating history for no. 2.

Most men would consider themselves unfathomably lucky to have dated even one of the women on this list. Even if you’re not a Yankees fan, it gives you a newfound respect for Jeter, doesn’t it?