When it comes to relationships, Madonna has had her fair share over the years.

Though she has only been married twice, the international pop icon has dated celebs from all walks of the industry, including rappers, dancers, fellow musicians, actors and more.

Who was Madonna married to?

Sean Penn

Sean Penn and Madonna first crossed paths on the set of her music video for “Material Girl” in February 1985 and tied the knot later that year in August in front of more than 200 guests in Malibu, California.

The “Vogue” singer filed for divorce two years later, and their split was finalized in 1989.

“There was no one direct incident leading up to this,” her rep told People at the time. “It was a series of cumulative pressures. There were many moments in their marriage when it was shaky, and Madonna was finally forced to face the reality of the situation — that they weren’t happy together.”

Guy Ritchie

Madonna started dating director Guy Ritchie after meeting at a party thrown by mutual friends Sting and his wife Trudie Styler in 1999. The pair wed in December 2000 in a private ceremony in Scotland and we married for eight years before announcing their plans to divorce in 2008.

Together they share one son, Rocco, born August 2000.

Who has Madonna dated?

Dan Gilroy

Madonna credited her shift in focus from dance to music to now ex-boyfriend and former bandmate Dan Gilroy, whom she met in 1979 at a party. The pair dated for about 18 months before going their separate ways.

“It was one of the happiest times of my life,” she told Rolling Stone in a 1984 interview. “I really felt loved. Sometimes I’d write sad songs and he’d sit there and cry. Very sweet.”

Jean-Michel Basquiat

The “Like a Virgin” singer briefly dated late artist Jean-Michel Basquiat in 1982 for a few months. While speaking with David Blaine for Interview Magazine in 2014, Madonna touched on their relationship and how in awe of him she was.

“Basquiat was my boyfriend for a while, and I remember getting up in the middle of the night and he wouldn’t be in bed lying next to me; he’d be standing, painting, at four in the morning, this close to the canvas, in a trance,” she recalled. “I was blown away by that, that he worked when he felt moved.”

Years after their split, Basquiat died of a heroin overdose in 1988. He was 27.

John ‘Jellybean’ Benitez

Madonna met DJ John “Jellybean” Benitez in 1983. Benitez produced her song, “Holiday,” but after less than two years of dating, the pair reportedly split in 1985.

Warren Beatty

Madonna met Warren Beatty on the set of the 1989 film Dick Tracy, in which Madonna portrayed a lounge singer while Beatty played the ritual detective. The pair started dating a year later in 1990 and broke up the following year.

Vanilla Ice

Madonna dated rapper Vanilla Ice (real name Robert Van Winkle), who is nine years her junior, began dating in 1991. The duo parted ways about eight months later in 1992.

“We would go to [the] movies. We had disguises. I had a mustache and a hat with hair coming down and she would go as an old lady,” the “Ice Ice Baby” artist recalled to George Stroumboulopoulos in a 2013 interview. “And we could walk in and the bodyguards would be like 20 feet behind, kinda looking like we’re nobody. And just walk in and go and see our movie and just have a good, normal … we’d do dinner that way and nobody would ever recognize us. It was the greatest.”

Tupac

Madonna and late rapper Tupac met in 1993 after being introduced by Rosie Perez, and dated in secret until their January 1995 split. The “California Love” rapper explained in a letter from prison why he broke up with the seven-time Grammy Award winner. TMZ published portions of the previously unseen letter in 2017.

Noting that he was angry after an interview Madonna did, in which she allegedly said, “I’m off to rehabilitate all the rappers and basketball players,” Tupac wrote, “Those words cut me deep seeing how I had never known you to be with any rappers besides myself. It was at this moment out of hurt and a natural instinct to strike back and defend my heart and ego that I said a lot of things … Can you feel me?”

He added, “In the time since, as you can see, I have grown both spiritually and mentally. It no longer matters how I’m perceived. Please understand my previous position as that of a young man with limited experience with an extremely famous sex symbol.”

Dennis Rodman

LOS ANGELES – APRIL 24 1994: Dennis Rodman #10 of the San Antonio Spurs is seen leaving the arena with Madonna after playing an NBA game against the Los Angeles Clippers at The Los Angeles Sports Arena on April 24, 1994 in Los Angeles, California. The Spurs defeated the Clippers 112-97.

Madonna and former NBA star Dennis Rodman briefly dated in 1994. Though the relationship was short-lived, Rodman looked back fondly at their romance in his 1996 memoir, Bad As I Wanna Be.

“We never had any problems,” he wrote at the time. “It was one of the easiest relationships I’d ever been in.”

Carlos Leon

The “Crazy for You” songstress started dating personal trainer Carlos Leon in 1994 but split in 1997. Together they share one daughter, Lourdes, who was born in October 1996.

Brahim Zaibat

Madonna met French model and dancer Brahim Zaibat in September 2010 after he performed at the launch of her Macy’s line, Material Girl. The pair, whose nearly 30 year age gap made headlines, dated for about three years before going their separate ways.

“She was just a woman almost like the others,” Brahim told OK! Magazine in 2012 of meeting the icon at her Macy’s launch. “An exceptional artist and world-famous, of course, but a woman first. I was just happy to meet her.”

Ahlamalik Williams

Madonna first met Ahlamalik Williams — who is 36 years her junior — when he was a dancer on her Rebel Heart tour in 2015. The pair sparked romance rumors in 2019, and although their relationship was mostly low-key, the choreographer made numerous appearances on Madonna’s Instagram during that time.

The duo dated for about three years before splitting in 2022.

Josh Popper

Madonna and trainer Josh Popper, who briefly appeared on Summer House, were rumored to have a fling in 2023. After appearing in photos on his Instagram in February that year, the two later shared a smooch on stage during her CelebrationTour in December. They appeared to go their separate ways at some point after that.

Who is Madonna Dating Now?

Akeem Morris

Madonna first met Jamaican soccer player Akeem Morris on the set of her Paper Magazine cover shoot in 2022; however, they didn’t spark romance rumors until nearly two years later the singer posted a since-deleted Instagram photo of the twosome canoodling on Fourth of July in 2024.

Morris was also spotted celebrating Madonna’s 66th birthday in Italy that same year, and a shirtless Morris was spotted in Madonna’s holiday post later in December.

As of June 2025, it is unclear if they are still together.