Derek Jeter is the King of Dating in the 2000’s, but he almost got dethroned…
Hall of Fame inductee Derek Jeter speaks during an induction ceremony at the Clark Sports Center on Wednesday, Sept. 8, 2021, at the National Baseball Hall of Fame in Cooperstown, N.Y. (AP Photo/Hans Pennink)

Derek Jeter is a legend both on the field and off it. I’ve often wondered if the Yankees great is better known for winning 5 World Series rings, or for dating the greatest string of A-List celebrities.

Before marrying his wife, Hannah, five years ago, Jeter had relationships with Minka Kelly, Mariah Carey, Jessica Biel, Jordana Brewster, Vanessa Minnilo, and Victoria’s Secret model Adriana Lima. Jeter was also rumored to have been involved with other models and entertainers, but I did not include them because those stories were never confirmed.

Jeter’s girlfriend list is arguably the greatest since actor Warren Beatty, who seemingly hooked up with every A-List star in his prime. This brought singer John Mayer to mind. He sang several hits in the early 2000’s, including “Your Body is a Wonderland” – which is rumored to be about his ex-girlfriend, actress Jennifer Love Hewitt.

Mayer also seriously dated singers Katy Perry, Jessica Simpson (who he called “sexual napalm”), Taylor Swift, actress Jennifer Aniston, and comedian Milana Vayntrub (who is best known as Lily in the AT&T commercials). Not bad for a guy who sounds like Kermit the Frog when he sings. Talented guitar player, though!

I asked my Twitter followers who is the 2000’s King of Dating: Jeter or Mayer? I provided the list of former girlfriends. Woke up this morning with over 200 votes… and it was tied! I re-tweeted the poll with just a few minutes left to see if the tie could be broken. Finally, Derek Jeter won with 51% of the vote.

Some of my favorite comments on Twitter, as to who won:

Tony – “Jeter. Mayer lost when Taylor Swift was thrown in.”

John – “The Mayer roster is too one dimensional, and he loses points for Taylor Swift.”

Joshua – “Other than Milana, it’s a Jeter win.”

D’Ante – “Jeter and it isn’t even close…Mayer not too shabby.”

Danny – “Mayer once described Jessica Simpson as “sexual napalm.” So, I’m gonna say Mayer… plus Lily, so it’s kind of a no-brainer.”

Brendan – “They’re both lists of gorgeous women. Derek was with Mariah Carey, though. He wins.”

We debated the dating lists within San Antonio Sports Star, and here too the vote was close. Personally, I give a slight edge to Jeter – but man, I’ve had a crush on Milana Vayntrub for years.

The people have spoken: Derek Jeter is this century’s number one playboy. John Mayer is still single, though, so he could still tilt the scales in his favor. One thing’s for sure – both Jeter and Mayer belong on the Mount Rushmore of Dating.

What do you think? Is Derek Jeter the GOAT when it comes to dating history? Reach out to Michael on Twitter @MikeESPNSA. You can listen to Michael on “Halftime” weekdays from Noon to 2 p.m. on 94.1 FM.