The New York native made a name for himself when playing for the New York Yankees from 2004 to 2013 before returning in 2015 for one more year. When he wasn’t making headlines for his big at bats, his relationship status was grabbing the attention of his fans.
After Rodriguez separated from his wife, Cynthia Scurtis, in 2008, after welcoming two daughters together, the MLB alum’s Hollywood flings became a more frequent occurrence.
Two months after announcing their engagement, Rodriguez posted a throwback video to his Instagram account, in which he gushed about the Grammy winner when he was still playing ball.
When asked by a reporter “what a dream date” would be for him in 1998, Rodriguez, quickly answered, “Jennifer Lopez. Hopefully you can find me a date with her.”
The sports star continued to gush about the Second Act star, including writing sweet Instagram tributes to Lopez on her birthday over the years.
“Every moment with you is magical. You are the greatest partner, the best mum, the most amazing performer,” he wrote in July 2020. “A role model. A hero. An inspiration. I’m so proud of you. I love you so much!”
Rodriguez and the Hustlers actress eventually called off their engagement in April 2021.
“We have realized we are better as friends and look forward to remaining so,” the former couple wrote in a joint statement at the time. “We will continue to work together and support each other on our shared businesses and projects. We wish the best for each other and one another’s children. Out of respect for them, the only other comment we have to say is thank you to everyone who has sent kind words and support.”
“I think I’m gonna make a wonderful partner or husband and father post-suspension, because of the lessons learned [from] my biggest mistakes,” Rodriguez said during an October 2022 interview with CNN, referring to his 2014 scandal in which he was penalized by the MLB for violating anti-doping regulations. “Post-suspension, I look at more the team-building, being a great father, being a son, being a friend, high character, loyalty, all those things.”
Scroll down to relive Rodriguez’s dating history — from musicians and Hollywood A-listers and beyond.
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