24 People You Forgot Madonna Dated

Ingrid Casares

Not only is Ingrid Casares one of Madonna’s BFFs, but multiple outlets, including DailyMail, claimed they were in a relationship from 1993 to 1994.

Bobby Brown

Bobby Brown revealed to UsMagazine, per Extra TV that he had a brief fling with Madonna. “We met through mutual friends,” he recounted. “One of her dancers was dating a friend of mine and I guess she told my friend that Madonna wanted to meet me. We ended up going down to the studio and the next thing I know, there was some strange things happening to me.”

Jenny Shimizu

Not only was Jenny Shimizu attached to Angelina Jolie for a few years, but she dated Madonna from 1993 to 1994. Shimizu revealed “She would book me on flights to any part of the world where she was on tour, just to sleep together. I was her sex slave,” per IBTimes.

Dan Gilroy

Back in 1980, musician Dan Gilroy was Madonna’s boyfriend during her early years in New York City as a struggling performer. The couple was a part of the musical group, Breakfast Club, where they had one hit single, “Right On Track.”

Jean-Michel Basquiat

Madonna dated artist Jean-Michel Basquiat, a protégé of Andy Warhol, when they were both rising stars in 1982. Unfortunately, they had a nasty breakup and they never buried the hatchet. 

“He wouldn’t stop doing heroin. He was an amazing man and deeply talented, I loved him,” said Madonna during an appearance on The Howard Stern Show, via ArtNet. “When I broke up with him, he made me give [the paintings he gave me] back to him. And then he painted over them black.”

Sean Penn

Madonna and Sean Penn loved hard and they fought hard. And any fan who has seen her documentary, Truth or Dare, knows the answer to this question: “Who has been the love of your life for your whole life?” She responded wistfully, “Sean. Sean.”

The duo was hounded by the paparazzi during the years they were married from 1985 to 1989 and Penn’s anger issues certainly didn’t help the situation, but they were doomed from the start because of their tabloid status. There were reconciliation hopes from fans in 2016 when he admitted, “Ah, I love my first wife very much,” to Stephen Colbert, but alas, it was not meant to be. 

John F. Kennedy Jr.

This was definitely an illicit affair. Even though Madonna was separated from Sean Penn in 1988, John F. Kennedy Jr. was involved with girlfriend Christina Haag— so the pop star and the Camelot heir kept their love on the down low. 

The six-month fling also didn’t have the blessing of JFK Jr.’s devoutly Catholic mom, Jackie Kennedy Onassis, who found Madonna’s wardrobe and accessorizing with crosses “sacrilegious,” according to Christopher Anderson’s book, The Good Son: JFK Jr. and the Mother He Loved. 

Esai Morales

Madonna reportedly had a short-lived fling with actor Esai Morales while they were filming Bloodhounds of Broadway. And yes, this was also during her separation from husband Sean Penn. 

Warren Beatty

Warren Beatty was 21 years her senior when they dated in 1989 and 1990 after meeting on the set of Dick Tracy. This is another relationship that gets summed up in one quote from her Truth or Dare documentary because they were very (we mean very) different personalities.

“She doesn’t want to live off-camera, much less talk,” Beatty says when Madonna refuses to talk to her doctor off-camera. “There’s nothing to say off-camera. Why would you say something if it’s off-camera? What point is there existing?”

Michael Jackson

When two global pop stars go to the 1991 Oscars together, it’s a night that no one will ever forget. Madonna never really kissed and told about their dates, but she sure did tease fans. 

“Michael [Jackson] was like, ‘Well, who are you going to go with?’” Madonna said in a vintage VH1 interview. “I looked at him and said, ‘I don’t know. You want to go?’ And he said, ‘Yeah, that’d be great.’ … And then, yes, he took me home. You wanna know what happened after that? I’m not gonna tell you.”

Chris Paciello

During Madonna’s Miami club days in the early ’90s, she dated former mobster Chris Paciello, who turned into a nightlife impresario with her former BFF Ingrid Casares. 

Tony Ward

Tony Ward might have been the start of Madonna’s preference for models as he worked for Calvin Klein and was a part of her controversial Sex book. 

Vanilla Ice

Tony Ward might not have been the only person she was dating during her time shooting Sex — it looks like Vanilla Ice overlapped with the model. The rapper was also a part of the book and called her “a great lover” to News Of The World, via IMDB. 

But Vanilla Ice wasn’t so pleased once the book was published. “But I broke up with her after she printed that book because I was hurt to be an unwitting part of this slutty package,” he said. “It was disgusting and cheap. We were in a relationship yet it looked like she was screwing all these other people.”

Tupac Shakur

It was reportedly Rosie Perez, who introduced Tupac Shakur to Madonna at Soul Train Awards in 1993, but this secret romance was doomed from the start. Many fans didn’t even know that the two superstars even dated until an apology letter written by Shakur was put up for auction in July 2017 — but it gave insight into their breakup.

The rapper struggled with the optics of a Black man dating a white woman since much of his music was about the Black experience. “For you to be seen with a black man wouldn’t in any way jeopardize your career,” he wrote, via TMZ. “But for me, at least in my previous perception I felt due to my ‘image’ I would be letting down half of the people who made me what I thought I was.”

Dennis Rodman

Sports fans know that with Dennis Rodman, any story is going to be wild — especially when it involves Madonna. He claims the “Like A Virgin” singer sent a private plane to Las Vegas, where he was gambling, and flew him to New York City because she was ovulating and wanted to have a child with him (we told you this story was wild). After the deed was done, he went straight back to the casino in Nevada. 

“I tried,” the former basketball player told The Breakfast Club, via Bleacher Report, that Madonna also allegedly offered him $20 million to get her pregnant. Um, OK. 

Carlos Leon

Carlos Leon was a celebrity fitness trainer when he met Madonna in 1995 and they were soon working out after hours. And that’s how Lourdes Leon came along in 1996. Even though the duo only stayed together until 1997, Carlos has been a constant presence in his daughter’s life and he’s maintained an amicable relationship with his ex.

“I’m forever grateful to [Madonna],” Carlos told People in 2011. “I have no regrets. I wouldn’t change anything. I got the best thing out of that relationship, and that’s my daughter. My daughter is everything to me.”

David Blaine

David Blaine and Madonna might seem like an odd match and it turns out, it wasn’t a match made in heaven. The duo had a rumored fling in 1998, but remained great friends throughout the years. The magician is the one who reportedly helped the pop star reconcile with oldest son Rocco in 2016 after a brutal custody battle with ex-husband Guy Ritchie, per Page Six.

Guy Ritchie

It was Sting who introduced Madonna to her second husband. She met director Guy Ritchie in 1999 and fell head over heels in love and welcomed son Rocco in August 2000. Their wedding followed in December at Skibo Castle in Scotland. 

In 2006, they adopted son David Banda from Malawi, but their marriage only survived another two years. It was a contentious divorce and Madonna later shared an intimate view to Newsweek about what happened her marriage to Ritchie.

“Because when you start off, everything’s great and lovely, and the person you’ve married is flawless, and you’re flawless,” she said. “Then time goes by, and you share a life, you have children, and there are cracks in the veneer. It’s not as romantic as it used to be.”

Alex Rodriquez

Well, well, well… Jennifer Lopez’s ex is also Madonna’s ex, except this was a rather sticky situation. As the Material Girl was rebounding from her divorce from Ritchie, A-Rod was still very married to wife Cynthia Scurtis when they began their affair in 2008.

It’s what ended the New York Yankees player’s marriage because his wife reportedly couldn’t take the public humiliation. “Cynthia is a strong person,” a source told People. “But a wife with two young children can only take so much.” Another insider added, “The embarrassment over Madonna was the last straw.”

Jesus Luz

Alex Rodriguez was the last celebrity Madonna was involved with because she switched up her dating strategy when she began a relationship with Brazilian model Jesus Luz. The 28-year age gap had every press outlet calling him her “boy toy,” but they did make it a year together. He reportedly dumped her because they didn’t have enough in common. 

Brahim Zaibat

The same year she split with Jesus Luz in 2010, Madonna decided that a 30-year age difference was even better in her relationship with dancer Brahim Zaibat. The duo lasted a solid three years as a couple and broke up in 2013. 

Timor Steffens

Six months after her split from Brahim Zaibat, Madonna took up with dancer and choreographer Timor Steffens. He also didn’t mind the 30-year difference in their ages one bit. “There is an age gap between me and Madonna, but I don’t notice it,” he explained to the Daily Mail. “My girlfriends have always been older than me and that’s how I like it. I learn a lot.”

They broke up shortly before her 56th birthday in 2014. 

Kevin Sampaio

Portugese model Kevin Sampaio also found himself dating Madonna when she was 58 years old — only a 27-year age difference. (You go, girl!) It was work that brought them together in 2015 when he starred in her “Bitch I’m Madonna” music video. It was a friendship that developed into a two-year relationship before they split in 2019. (And yes, he’s a twin. That’s Kevin on the right.)

Ahlamalik Williams

Madonna’s current boyfriend is dancer and choreographer, Ahlamalik Williams, who has worked on two of her tours: 2015’s Rebel Heart Tour and 2019’s Madame X Tour. They began dating that same year and their love has been going strong throughout the pandemic. It’s no surprise that they also have a 36-year age gap because Madonna knows what she likes — and they also have the support of Ahlamalik’s dad, Drue Williams “Love has no age,” he told TMZ. “My son is livin’ la vida loca, and I’m just happy for him.”