Dive into Madonna's romantic saga
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The saga began with Dan Gilroy, whom Madonna first became involved with in 1979 after meeting him at a New York party. Gilroy was also instrumental in sparking her passion for music.
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In 1982, Madonna entered into a relationship with acclaimed artist Jean-Michel Basquiat. However, Basquiat's tragically short life, marked by addiction, led to their split.
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Madonna met John "Jellybean" Benitez in 1983, but their relationship didn't last, concluding in 1985.
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In 1985, Madonna crossed paths with Sean Penn on the set of her legendary "Material Girl" music video. Six months later, they married on Madonna's 27th birthday, a day before Penn's 25th.
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Penn’s possessiveness and volatility led Madonna to file for divorce in January 1989, thus ending their tumultuous marriage.
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Madonna engaged in a brief dalliance with model and actor Tony Ward in 1990, who featured in her provocative music video for “Justify My Love.”
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Madonna and Warren Beatty first met on the set of the movie “Dick Tracy.” Their romance took off in 1990 and continued for a total of 15 months.
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Madonna's bodyguard, Jim Albright, confessed to a clandestine romance with Madonna in February 1991, as revealed by Jim in a 2001 interview.
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In 1991, Madonna briefly dated rapper Vanilla Ice, a relationship that only spanned 8 months. Ice later revealed that Madonna seemed to still harbor feelings for Penn.
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Madonna was briefly involved with rapper Tupac Shakur around 1993, a relationship that was cut short by Tupac's worries about how it might affect his public persona.
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Madonna often flirted with John F. Kennedy Jr. via fax and phone calls. However, it's generally believed that their relationship never transcended flirting.
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In 1994, Madonna encountered personal trainer Carlos Leon in Central Park. The pair welcomed a daughter in 1996, but they went their separate ways in 1997.
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Madonna's life shifted gears in 1999 when she met director Guy Ritchie at a party. Their relationship blossomed over several months and they welcomed a son in August 2000.
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Ritchie proposed to Madonna merely six days after their son's birth, and they tied the knot on December 22, 2000. However, their marriage came to an end in October 2008.
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According to the lawyer of Yankees player Alex Rodriguez’s ex-wife, Madonna was allegedly the catalyst for their divorce, having reportedly been involved with Rodriguez while still married to Ritchie.
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In September 2010, Madonna embarked on a relationship with French model and dancer Brahim Zaibat. However, after three years, they broke up, citing "busy schedules" as the reason.
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After parting ways with Zaibat, Madonna briefly dated choreographer Timor Steffens in 2014. Their romance fizzled out shortly after Steffens spilled the beans to a tabloid about their relationship.
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In 2019, Madonna began dating dancer and choreographer Ahlamalik Williams, who is 36 years her junior. However, they called it quits in April 2022.