The Truth About Derek Jeter's Dating History

When it comes to Derek Jeter's dating history, he consistently batted way over .300. The former NY Yankees shortstop-turned-business mogul-turned-Miami Marlins co-owner wined and dined some of Hollywood's hottest — or was alleged to, anyway.

Unlike his fellow former Yankee, Alex Rodriguez, Jeter was conscious of always being the star of the baseball field, not the tabloids. He kept his private life strictly private. As per Bleacher Report, he was all about the game, not seeking publicity outside of that. 

Baseball is a sport packed full of scandals and controversies. Still, somehow, over the years, Jeter managed to escape all and any — earning himself the nickname of "Mr. Clean" (via "You have to assume that everything you do is public knowledge," Jeter told Sports Illustrated shortly after announcing his retirement. "Everything. Because now everyone is a reporter. Everyone is a photographer. Someone can take a picture and make a story, which has happened plenty of times, and twist it and turn it any way they want to. You used to be able to go out ... it's all I've known. I've been here since I was 20."

So exactly how "clean" was "Mr. Clean" when it came to his bachelor days' scoring position? Tie up your cleats, folks — we're going to hit for the cycle with the truth about Derek Jeter's dating history.

Mariah Carey

When Mariah Carey first met Derek Jeter, she was still in a relationship with her first husband, Tommy Mottola. According to Carey, their marriage was far from a happy one. "Many reasonable people have questioned why I married Tommy. But none of them questioned the decision more than I did," she wrote in her memoir, "The Meaning of Mariah Carey." The singer claims that Mottola was emotionally abusive and controlling — allegations that the music world head honcho has vehemently denied (via Billboard).

Either way, Carey says she had an escape bag packed and ready just in case she found the opportunity to flee. And that opportunity came in 1998, in the form of a 6' 3" New York Yankees baseball star. Despite only dating for a short time, Derek Jeter swept Carey off of her feet. She told Oprah Winfrey that he proved to be the "catalyst" for her eventually leaving Mottola.

"It was so sensual," Carey wrote about their brief affair (via Page Six). "Everything was so new and sweet, down to the smooth texture of his honey-dropped skin. It was so heady, so intoxicating, and I was so vulnerable. I was in touch with a fire I didn't know I had inside." After telling Vulture that she and Jeter started flirting via text after meeting at a dinner party, Carey admitted that he was the inspiration for two of her songs, "The Roof" and "My All."

Bridget Hall and Lara Dutta

When you're a multi-millionaire baseball ace, it's not too much of a seventh-inning stretch to catch yourself a smoking hot hookup. However, Derek Jeter hit it out of the park by allegedly dating not one but two top models during the early aughts.

Jeter purportedly launched his model girlfriend run by hooking up with Sports Illustrated cover girl Bridget Hall. As per Your Tango, the couple got together for a hot minute, or two, in early 2000. Neither spoke publicly about their rumored romance and were never photographed together — so, as is the case with much of the notoriously private Jeter's private life, it's speculative. One thing's for sure, though — they definitely would have made a priddy pair.

According to Fox Sports, Jeter also saw Lara Dutta in 2000 — although they apparently went on to date for a year. The Indian-born model had recently won the coveted title of Miss Universe when she reportedly started seeing the star athlete. The couple kept their alleged romance on the down low, never publicly confirming they were dating and not being spotted out and about on the town together. However, they were caught on camera cozying up courtside at a New York Knicks and Vancouver Grizzlies game at Madison Square Garden in November 2000. As a New Yorker, it's pretty much a given that Jeter would have been thrilled at the result: The Knicks won 97-72 (as per ESPN).

Joy Enriquez and Jordana Brewster

Derek Jeter continued to sow his wild oats throughout the early aughts. However, he temporarily paused his model spree and dipped his toe into the Hollywood pool for some new, nubile dating opps.

Fresh off his alleged year-long relationship with Lara Dutta, Jeter reportedly enjoyed a fling with the actor and singer Joy Enriquez in August 2001. Per the New York Post, the couple was introduced by Alex Rodriguez, who was casually dating the "7th Heaven" star at the time. "Joy wasn't exactly sure of Alex's intentions, but she and Derek just couldn't keep their eyes off each other," a source claimed. According to The Post, Enriquez and Jeter's dates consisted of going out to games and dinner. Friends claimed they were an item, despite living on opposite coasts at the time. 

After getting his first taste of Hollywood, Jeter moved on to reportedly date Jordana Brewster. The Panama-born actor appeared in a total of six "Fast & Furious" movies in addition to "The Texas Chainsaw Massacre: The Beginning" (via IMDb). Luckily for Jeter, the romance didn't end in bloodshed. Instead, they went on to see each other for a year, from 2002 – 2003. They were first spotted together publicly when they went out clubbing to celebrate Jeter's 28th birthday in July 2002. Before long, Brewster became a fixture at Jeter's side as they cheered on his beloved Lakers, sitting courtside.

Vanessa Minnillo

Derek Jeter returned to his model-love roots when he started dating Vanessa Minnillo in 2003. The Filipino-American model was crowned Miss Teen USA in 1998. She went on to host the Miss Universe pageant before becoming a correspondent for "Entertainment Tonight" and a veejay for "Total Request Live."

According to E! Online, Minnillo dated Jeter, AKA the King of New York, off and on for "several years" before they both finally went their separate ways. Given the timing of their final parting, it looks like she very likely found a boy band member-turned-reality TV star. Neither Minnillo nor Jeter has ever publicly spoken about their relationship or the reason behind their split. 

However, as per Insider, Minnillo met 98 Degrees star Nick Lachey on the set of "Total Request Live" in 2006. It was a year after Lachey had announced his split from then-wife of three years, Jessica Simpson (via People magazine). Minnillo and Lachey became hot and heavy fast before splitting briefly in 2009. They went on to marry in 2011 and now have three children together.

Jessica Alba

Derek Jeter and Jessica Alba's alleged relationship can definitely be filed under R for rumored. As per the New York Daily News, Alba and Jeter supposedly hooked up in 2004. Jeter was on a break from his on-again-off-again girlfriend Vanessa Minnillo at the time.

Neither has spoken about any romantic interactions — and they were never photographed together, so there's no actual proof of any kind. However, there's reportedly a reason there's no evidence of so many of Jeter's alleged rendezvous. According to the New York Post, to ensure his reputation remained sparkling clean, Jeter would allegedly smuggle his bevy of beauties in and out of his palatial Trump World Tower bachelor pad — via a "back-door entrance" to avoid paparazzi. "He normally doesn't go out with girls," a source said. "He will have them come to his house. He'll have cocktail parties. His friends invite girls they think he'll be interested in."

Jeter allegedly made sure that the lucky ladies never left empty-handed. The Post claims he would "[send] them home alone with gift baskets of autographed memorabilia." It's rumored that Jeter also gave Alba a parting gift — although it's definitely not one that you could sell on eBay. The rumors behind the alleged "gift" are totally unsubstantiated and stem from a random gossip blog. So as per the NY Daily News, you can turn to trusty old Google if you want to find out more.

Vida Guerra

Derek Jeter managed to fit another fling in during his on-off relationship with Vanessa Minnillo. According to The Bleacher Report, Jeter dated Cuban-born glamour model Vida Guerra for a short time during 2005. Guerra was voted "Model of the Year" by FHM in 2004. She also parlayed her talents into the world of rap, appearing in music videos for Diddy, Nelly, Frankie J, and Kanye West (via Latin Times).

As is usually the case with the notoriously publicly guarded Jeter, there's no credible info out there regarding his relationship with Guerra and no photos of them together. But, given her line of work, it's no surprise that there are plenty of pictures of Guerra out there — and a lot of them are decidedly NSFW. When she's not being paid to model, Guerra usually shows off her God-given gifts on her Insta feed, much to the delight of her 620,000 plus followers.

However, following the news of Jeter's engagement to now-wife Hannah Davis, Guerra kindly provided TMZ with some bountifully bodacious booty pics. Guerra announced that she is "on a mission" to show the world that she's the sexiest of Jeter's stable of sexy exes. "Hannah is Derek's type for sure; he's always liked tall girls," Guerra told TMZ. "But she was like seven when him and I dated. Curves are in — and I have all of those." And, yep, girlfriend's definitely got back.

Jessica Biel

There may be no objective evidence of a relationship between Derek Jeter and Jessica Alba. However, it's a different case when it comes to Jessica Biel. Jeter and Biel dated for an undisclosed period during the latter part of 2006 into early 2007.

According to People magazine, the couple was spotted getting hot and heavy in Las Vegas during the post-Thanksgiving weekend. It appears that Jeter and Biel couldn't keep their hands off each other, showing off their PDA-packed pairing all over Sin City. They were caught making out at Wynn Las Vegas' Tryst nightclub as fellow Yankees A-Rod and Jason Giambi looked on. They were spotted hitting the blackjack tables and dining with friends at the Palms Casino Resort. And, they got down at the Hard Rock's Body English club, where an onlooker claims they appeared "very lovey-dovey."

Jeter and Biel even took their romance overseas in January 2007. Pop Sugar published photos of the two frolicking in the surf in Puerto Rico. After an exhausting day in the sun, the couple retreated to their "four-star resort" for some Netflix and chill, probably (via New York Post). Which begs the question — why only four-star? Couldn't Jeter afford to splash out on a five-star resort? Perhaps that's why Biel started dating Justin Timberlake that very same month.

Adriana Lima

Derek Jeter really upped his model dating game when he reportedly started hooking up with Adriana Lima. The Brazilian-born supermodel is Victoria's Secret's longest-lasting catwalk queen, having started working with the lingerie giant back in 1995. Lima's stunning good looks have helped earn her some serious bank. Forbes ranked the Maybelline spokesperson as the world's fourth highest-paid model in 2017 — with an estimated fortune of $10.5 million. That's still a considerable way off of Jeter's estimated net worth of $200 million (via Celebrity Net Worth) but not to sniffed at for sure.

As per Sport One, Jeter and Lima were alleged to have dated for several months during 2006. Once again, as is the usual case with Jeter's love life, everything was kept decidedly on the down-low, with neither speaking publicly about any romance. However, according to Sport One, although the two never confirmed they were an item, some insiders claimed they were dating.

There is some kind of (sort of) evidence, though — well, in the very loosest sense. Jeter and Lima were spotted hanging out together at an event once sometime during 2006. Page Six has a photo of the couple looking decidedly cozy, with matching tans no less — and Lima's arm slung around Jeter's shoulder as she grins somewhat crazily at the camera.

Rachel Uchitel

For a brief time during 2008, Derek Jeter dated Rachel Uchitel. Yes, that Rachel Uchitel. At the time, she was living in Las Vegas, running VIP front of house for a friend's club.

Uchitel spilled the tea to Heather McDonald in an interview for her "Juicy Scoop" podcast. Uchitel explained that she'd fled Manhattan following her marriage breakdown. She'd rushed into matrimony while still grieving her fiancé — who was killed on 9-11 — a tragedy that altered her life forever. "There was something that changed in that moment," Uchitel said. "I was no longer a little girl. I was ... I had to protect myself. I didn't believe in fairytales anymore."

Uchitel shared that she'd landed in Vegas during a road trip she'd taken because she wanted to go find "a love story." Sadly for Uchitel, instead of a love story, she found herself at the center of one of sporting history's biggest sex scandals after engaging in an affair with Tiger Woods. And, it was all thanks to Jeter — kind of — as he (unwittingly) facilitated their meeting. "I was dating Derek Jeter, and Tiger was sleeping over at Derek's house, and so he was the guest in the guest bedroom, and he was just a buddy," Uchitel shared. "And I remember he was, we were opening up Derek's window, and he was smoking a cigar out the window or something, and we just became friendly. And so that's how I originally met him."

Minka Kelly

After decades of living the bachelor life and a list of seemingly endless serial hookups — secret or otherwise — it finally looked like Derek Jeter had met "the one" in 2008. Sometime after his brief fling with Rachel Uchitel ended, Jeter started dating Minka Kelly.

As per the norm for Jeter, it was all kept decidedly on the "hush-hush." Neither spoke publicly about their relationship or even confirmed they were dating. But, over three years, they were snapped, engaging in numerous PDAs. Jeter and Kelly were photographed locking lips on the streets of "Gay Paree." Seriously smooching on the baseball field. Gazing adoringly at each other as they hung out at various sporting events around the country. Even basking in the glory together on the Yankees World Series victory parade float in November 2009.

The "Friday Night Lights" actor appeared in her baseball boo's 2011 HBO documentary "Derek Jeter 3K," and it was clear there was a strong connection between the two. The couple became so close, there was even speculation that they were heading for a trip down the aisle — although Kelly's rep denied the reports (via Page Six). But then, shortly after the release of the documentary, just like that, it was over. Gossip site Just Jared was first to report the split — then Kelly's rep confirmed to People magazine that the previously never-confirmed coupling was a strikeout.

Wife Hannah Davis

In 2012, Derek Jeter met Hannah Davis, who would become his wife and children's mother. Yet again, Jeter managed to keep their romance relatively out of the press — despite the pair being spotted together in various cities across the U.S. (via Page Six). And, yet again, neither spoke publicly about their relationship or confirmed they were dating.

However, everything changed in 2015 after Jeter let slip on his website, The Players' Tribune, that his "fiancée" had bought him a dog for Christmas. Eight months later, the Sports Illustrated model went from fiancée to wife. According to E Online, they married in July 2016 at Meadowood Napa Valley Resort in St. Helena, California. The bride wore not one but two different stunning Vera Wang gowns — because, hey, why not? And, in typical Jeter low-key fashion, there were fewer than 100 guests.

Nowadays, Mr. and Mrs. Jeter live a quiet life (of course!) in Florida with their daughters, Bella Raine and Story Grey. "We're enjoying life and raising our family here," Jeter told Haute Living. And Hannah offered some insight into why the notorious bachelor finally felt ready to hang up his dating cleats. "We met at the right time," she wrote on her hubby's website. "To me, what matters in a relationship is being at the same place in your lives. And right from the start, I could tell that the timing of Derek's life and mine were aligned."