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.
Brewster, known best for The Fast and the Furious series and cult classic The Faculty, was one of Jeter's first celebrity girlfriends. The pair dated in 2002 and 2003. (Image source/Twitter)
Soon after winning Miss Universe in 2000, Dutta began dating the Yankee captain. Least surprising thing ever. (Image Source/Twitter)
Mariah Carey was one of Jeter's first celebrity flings. It also may have been the only time he dated a bigger star than himself. (Image Source/Twitter)
This was a short fling many years ago. But Guerra was once one of the top models in the world, so it's not a shock that she had a fling with the Yankee captain. (Image Source/Twitter)
It's tough to confirm the details of this relationship, but would it surprise anyone that Jeter was once involved with arguably the top model of all time? (Image Source/Twitter)
To this day, both parties deny hooking up. Both there have always been whispers of a fling between Jeter and Dwayne Wade's current wife back in 2007. (Source Image/Twitter)
Uchitel is best known for being a mistress of Tiger Woods. But there are widespread rumors that she also had a fling with Jeter. (Image Source/Twitter)
This one's a little complicated. It's believed that Enriquez met Jeter while dating A-Rod, and they may have broke up with A-Rod to date Jeter. That may not be the real story, but it wouldn't be that shocking, would it? (Image Source/Twitter)
Another model? Shocking. This one's not exactly confirmed, but there are rumors that Lima dated Jeter in 2003. Being a model, she's exactly his type, so it's probably true. (Image Source: Twitter)
Many years ago, Alba reportedly had a fling with Jeter. It's not exactly confirmed, but it's a safe bet. (Image Source/Twitter)
This is another fling that both parties have declined to confirm. But back in 2004, Jeter and ScarJo were frequently spotted together. (ImageSource/Twitter)
Before marrying Nick Lachey, this former Miss Teen USA was on again and off again with the Yankee captain from 2003 and 2006, making her one of Jeter's more serious relationships. (Image Source/Twitter)
Before settling for Justin Timberlake, Biel had a fling with Jeter for a few months around 2006 and 2007. (Image Source/Twitter)
Kelly may be the one that got away. She almost tamed the King of Flings, dating him from 2008 to 2011, with a brief reunion in 2012. But alas, it wasn't meant to be. (Image Source/Twitter)
If dating is a game, then Davis is the winner. The former Sports Illustrated swimsuit model married Jeter in 2016, and in a matter of months, the new Mrs. Jeter announced she was pregnant (Image Source/Twitter)
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?