father of three has lived in the spotlight since he began playing for the New York Yankees in 1995 aged 20. While fame opened many opportunities for the former baseball player, it also exposed his love life. Though now retired fans still want to know more about Derek Jeter's dating history.
Derek briefly dated music icon Mariah Carey in the late 90s when the two were one of the biggest stars of that time. Their relationship made headlines since the Grammy Award winner was still married to music executive Tommy Mottola.
During an interview, the singer revealed to Oprah Winfrey that her brief relationship with Derek was significant as it helped her walk away from her toxic relationship with Mottola.
The "We Belong Together" singer revealed to the talk show host that Derek was the "catalyst" for her divorce from Mottola, whom she termed controlling, admitting that she felt like a prisoner while living with him. Even so, their relationship was brief( from 1997 until 1998).
The former New York Yankees reportedly dated Dutta, an Indian model, and actress who won Miss Universe 2000 Pageant, for about a year. According to reports, Derek pursued the "Bell Bottom" actress after he saw her on an episode of "Live with Regis & Kathie Lee."
Though it's unclear when they began dating, they were spotted together at the New York Knicks-Vancouver Grizzlies game at Madison Square Garden in January 2000.
New York Yankees' shortstop Derek Jeter and Lara Dutta (center), at Madison Square Garden on January 01, 2000 | Source: Getty Images
Derek reportedly dated singer and actress Enriquez in 2001. Enriquez met Derek through his friend Alex Rodriguez, a former baseball player playing for Texas Rangers. According to reports, Rodriguez introduced Enriquez, who he was casually dating, to Derek when they attended an All-Star Game in Seattle, and the two hit it off.
A friend of Enriquez's revealed that she and Derek couldn't keep their eyes off each other. The two reportedly went out several times after the All-Star Game.
Joy Enriquez attends the Walt Disney Picture's Video Premiere of Lady and the Tramp II: Scamp's Adventure February 18, 2001, in Los Angeles, CA. | Source: Getty Images
The two reportedly dated for a year and were publicly spotted together for the first time when they went clubbing to celebrate the baseball legend's 28th birthday in 2002. Soon after, the pair were spotted watching a Lakers game together.
Derek Jeter and actress Jordana Brewster sit courtside on December 19 2002, at Continental Arena in East Rutherford, New Jersey. | Source: Getty Images
The New York Yankees alumni reportedly dated actress, TV host, and former beauty queen Vanessa Lachey for almost three years. The two were in an on-and-off relationship from 2003 to 2006.
Nothing substantial came out of their relationship, and the two went their separate ways. Vanessa found love again and has been happily married to singer, actor, and TV host Nick Lachey since July 2011. The couple shares three children.
Derek was rumored to be dating "The Avengers" actress Scarlett Johanson in the early 2000s. Even though the two were reportedly seen leaving a Christmas party together, the award-winning actress denied the dating rumors.
Scarlett Johansson at the Mann Village Theater on August 4, 2008, in Westwood, California. | Source: Getty Images
Derek reportedly dated Cuban-born-American model Guerra in 2005. When Derek proposed to his current wife, Davis, in 2015, Guerra told TMZ that she was happy for the legendary shortstop. She told the publication that Derek was finally living his dream. She said:
"He said once he retired, he wanted to get married, so he’s living his dream. He’s really an awesome person, and I wish him all the best."
Vida Guerra at the 20th Annual Soul Train Music Awards on March 05, 2006 | Source: Getty Images
Jessica Biel and Derek reportedly dated for a few months in 2006. According to reports, the actress and Derek were spotted getting cozy and publicly displaying affection while enjoying a weekend in Las Vegas.
An onlooker also spotted the two at Social Hollywood in November of the same year, noting that Biel and Derek looked like they were on a date.
Jessica Biel appears on NBC News' "Today" show on December 08, 2011 | Source: Getty Images
When asked about his relationship status, Derek later revealed to PEOPLE that he was single. The following year, Biel began dating her now-husband, singer-songwriter and actor Justin Timberlake.
Actress Minka Kelly and Derek Jeter at the USTA Billie Jean King National Tennis Center on September 4, 2010, in New York | Source: Getty Images
TV personality Tyra Banks, actress Jessica Alba, Brazilian supermodel Adriana Lima, TV presenter Rachel Uchitel, and actress Gabrielle Union were all rumored to have dated Derek.
Still, all these rumored relationships were not confirmed. During an interview, Union addressed the rumors, stating that if she had dated Derek, she would announce it to the world.
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