Madonna Dating History: A Walk Through Her Past Relationships

How many men did Madonna date - List History

Madonna, the ever-reigning Queen of Pop, has had quite the journey when it comes to love. Her romantic escapades have been as diverse and captivating as her music, spanning across decades and involving some of the most intriguing personalities of Hollywood.

Her first walk down the aisle was with the fiery Sean Penn back in the mid-80s. Their union, however, was short-lived, ending in 1989. The second time Madonna said ‘I do’ was to the British filmmaker Guy Ritchie in 2000. This relationship too, unfortunately, didn’t stand the test of time and they parted ways in 2008.

Madonna’s love life has never been confined to her marriages. She’s had a fascinating array of romances, from the legendary Tupac to the eccentric Dennis Rodman, and the charismatic Warren Beatty, to name a few. Recently, the rumor mill has been buzzing with whispers of a possible romance with Josh Popper, the star of Summer House.

Despite her bold and unapologetic persona, Madonna isn’t immune to regrets. In a candid Q&A session on YouTube in 2022, she confessed to a fan that her two marriages were perhaps not her best decisions. Her response was swift and unambiguous: “Getting married. Both times!”

Adding another layer of intrigue to her persona, Madonna stirred up a storm in October 2022 with a TikTok video that hinted at her coming out as gay. However, she has yet to openly discuss her sexuality.

@madonna♬ original sound – nudy georges


So, there you have it – a whirlwind tour of Madonna’s romantic history, as colorful and unpredictable as the pop icon herself.

Why is Madonna so famous?

After her stint with bands like the Breakfast Club and the Emmys, Madonna took a bold step and embarked on a solo journey. Her debut single, ‘Everybody,’ hit the airwaves in October 1982, marking the beginning of an illustrious career. However, it was her 1983 release, ‘Holiday,’ that truly catapulted her into the limelight, earning a coveted spot on the US Billboard Hot 100.

From that point forward, Madonna’s career was a meteoric rise to stardom. She churned out hit after hit, earning her the well-deserved title of ‘Queen of Pop.’ Albums like ‘Like a Virgin,’ ‘Like a Prayer,’ ‘Ray of Light,’ ‘Music,’ ‘Erotica,’ ‘Bedtime Stories,’ and ‘Hard Candy’ consistently topped the charts, solidifying her status as a music industry powerhouse.

But Madonna’s influence extended beyond her chart-topping hits. She revolutionized the music industry, particularly for women artists. Known for her innovative approach to music production, songwriting, and visual presentation, Madonna continually pushed the boundaries of mainstream music, challenging norms and setting new standards.

Madonna’s impact has been felt across the 20th and 21st centuries, making her one of the most influential figures of our time. Her songs often tackled controversial themes, including social-political issues, sexuality, and religion. While these themes stirred controversy, they also garnered critical acclaim, reflecting Madonna’s fearless approach to music and her commitment to using her platform to address important issues.

Her Dating List

1. Dan Gilroy

Her journey from dance to music was catalyzed by a pivotal figure in her life – her then-boyfriend, Dan Gilroy. In a 1984 Rolling Stone interview, she shared how a chance meeting with Gilroy at a 1979 party led her to an abandoned synagogue in Queens, New York, where he and his brother resided. It was there that Gilroy handed her a guitar, tuned to an open chord, igniting a spark in Madonna that would change the course of her career. She started to shift her focus from dance to music, reducing her dance classes to dedicate more time to singing.

Her career took her to Paris, where she worked as a background singer and dancer for Patrick Hernandez. Despite her professional success, she felt isolated and invisible. It was Gilroy’s letters, filled with humor and affection, that kept her spirits high. She fondly recalled how his letters, often decorated with an American flag and playful messages, made her feel cherished and missed.

When illness forced her to return to the U.S., she reconnected with Gilroy and embarked on a period of “intensive musical training.” She described this time as one of the happiest in her life, filled with love, music, and emotional connection.

Madonna and Gilroy’s collaboration extended to his band, the Breakfast Club, where she began to play drums. She spent so much time with them that she eventually asked to move in, a request that was humorously deferred to Gilroy’s brother, Ed.

However, Madonna’s ambition to be the band’s lead singer caused friction between her, Gilroy, and his brother. This tension, coupled with her intense drive to succeed, led her to leave both the band and her relationship with Gilroy. She admitted to Rolling Stone that she was more goal-oriented and commercially driven than they were, and she capitalized on their knowledge to further her own career. This marked a turning point in Madonna’s life, as she set out to pursue her singing career full-time

2. Jean-Michel Basquiat

Jean-Michel Basquiat

In 1982, Madonna found herself in a relationship with the renowned artist Jean-Michel Basquiat. She was deeply moved by his unwavering dedication to his craft. In a 2014 Interview magazine feature, she reminisced about waking up in the middle of the night to find Basquiat painting, completely engrossed in his work. This image of him, standing inches away from the canvas in a trance-like state at four in the morning, left a profound impression on her.

However, their relationship was not without its challenges. In a 2015 interview with Howard Stern, Madonna revealed that their romance was brief, largely due to Basquiat’s battle with addiction. This struggle tragically claimed his life in August 1988, when he was only 27 years old.

She spoke fondly of Basquiat, describing him as an “amazing man” and “deeply talented.” She expressed her love for him, but also shared a poignant detail about their breakup. When their relationship ended, Basquiat asked for all his paintings that he had given her to be returned. In a symbolic act of closure, he painted over them in black, erasing the colorful traces of their shared past.

3. John “Jellybean” Benitez

John -Jellybean- Benitez

In 1983, Madonna’s path crossed with DJ John “Jellybean” Benitez, who later produced her hit song “Holiday.” The chemistry between them was undeniable, and they soon started dating. Those close to Benitez believed that their relationship was more than just a casual fling. Rumors swirled about an engagement, and the couple reportedly moved in together.

However, their relationship hit a snag when Madonna was rumored to have had an encounter with journalist Steve Neumann, who was dating her friend Erika Belle at the time.

A friend of Benitez’s shared with PEOPLE that Benitez was deeply in love with Madonna. They made a great team, but it was clear that Madonna was the one calling the shots. The friend described Madonna as a diva who loved to be the center of attention.

Their romance came to an end in 1985, coinciding with Madonna’s meeting with Sean Penn, marking the end of one chapter and the beginning of another in Madonna’s romantic journey.

4. Sean Penn

Sean Penn

She and Sean Penn’s whirlwind romance began in February 1985, when they met on the set of her iconic “Material Girl” music video. Their connection was instant, and they tied the knot just six months later, on Madonna’s 27th birthday, a day before Penn turned 25.

She once described Penn as being so similar to her that he felt like her brother. Their temperaments were alike, which she admitted might not always be conducive to a harmonious relationship. Their professional and personal lives intertwined when they co-starred in the 1986 film, “Shanghai Surprise.”

However, their marriage was far from smooth sailing. Tensions began to surface in April 1986 when Penn reportedly attacked songwriter David Wolinski for speaking to Madonna. This incident, which resulted in a fine and probation for Penn, was a significant strain on their relationship.

Penn’s jealousy further complicated matters. He was suspicious of model and singer Nick Kamen, who was collaborating with Madonna on a track, despite her denials of any affair.

In December 1987, Madonna filed for divorce, citing “cumulative pressures” and the realization that they weren’t happy together. She briefly withdrew her divorce filing, but by January 1989, she filed for divorce again, this time for good.

Despite their tumultuous past, Madonna and Penn have maintained a friendly relationship. In December 2016, Madonna even confessed that she was “still in love” with Penn, jokingly offering to remarry him if he bid $150,000 in a charity auction.

5. Tony Ward

Tony Ward

In 1990, Madonna found herself in the arms of model and actor Tony Ward, who shared the screen with her in the music video for “Justify My Love.” This video, known for its provocative content, was deemed too risqué by MTV and subsequently banned.

However, Madonna and Ward’s romance was fleeting. In 1991, PEOPLE reported a curious turn of events. Ward, it seemed, had quietly married his old flame, Amalia Papadimos, in a swift Las Vegas ceremony on August 21, 1990. Intriguingly, this was after he had started dating Madonna. Whether it was a coincidence or not, Ward’s sudden marriage appeared to coincide with his departure from Madonna’s side.

6. Warren Beatty

Warren Beatty

She and Warren Beatty’s paths crossed in 1989 on the set of the film “Dick Tracy.” Beatty, who was 21 years Madonna’s senior, played the titular detective, while Madonna portrayed the lounge singer Breathless Mahoney. Their on-screen chemistry spilled over into real life, and they began dating in 1990, a relationship that lasted around 15 months.

Beatty spoke highly of Madonna in a 2016 interview with PEOPLE, describing her as a “huge personality,” diligent, disciplined, and a spectacular performer. He referred to her as a “phenomenon.”

However, their relationship was not without its challenges. One point of contention was Beatty’s involvement in the documentary “Madonna: Truth or Dare.” Beatty initially did not want to appear in the film, but Madonna retorted, “Why would I want you in it?” Eventually, Beatty agreed to participate, on the condition that he could approve the footage featuring him.

Despite their initial compromise, their differing views on fame and publicity ultimately led to their breakup, which occurred shortly after “Dick Tracy” was released in theaters.

7. Michael Jackson

Michael Jackson

In a move that sent shockwaves through the entertainment world, the Queen of Pop, Madonna, arrived at the 1991 Oscars with none other than the King of Pop, Michael Jackson. This pairing of music royalty was the talk of the town, but insiders told PEOPLE that it was more of a publicity stunt than a romantic outing.

Despite the buzz around Madonna and Jackson’s appearance together, it seems that the spotlight wasn’t enough to keep Madonna’s attention. Once the cameras were off, she reportedly spent time with her then-boyfriend, Warren Beatty, further fueling the speculation that her Oscars date with Jackson was more about making headlines than kindling a romance.

8. Jim Albright

Albright alleged that Madonna had never been faithful to one man, a fact she herself admitted to him. He concluded, “She is only loyal to herself.”

Jim Albright began his relationship with Madonna in a professional capacity as her bodyguard. However, in 2001, he revealed that their relationship evolved into a secret love affair in February 1991, which lasted for three years. At the time their romance began, Albright was in a relationship, and he noticed that Madonna seemed to pull away once he ended his relationship to be with her.

When Albright stepped down from his role as Madonna’s bodyguard in 1993, their relationship deepened. He noted that Madonna would speak to him every day, and their bond grew so strong that they even considered marriage. However, Madonna’s insistence on a prenuptial agreement, which Albright refused, put a damper on their plans.

Albright claimed that Madonna’s insecurities and jealousy escalated over time. He alleged that she had affairs with various athletes and celebrities, including Ingrid Casares and comedian Sandra Bernhard. Despite Madonna’s supposed infidelity, it was only when Albright confessed to having a fling that Madonna ended their relationship.

9. Vanilla Ice

Vanilla Ice

In 1991, Madonna entered into a relationship with rapper Vanilla Ice, who was nine years her junior. Their romance, which lasted for eight months, was marked by a playful sense of adventure. In a 2013 interview with George Stroumboulopoulos, Vanilla Ice (whose real name is Robert Van Winkle) fondly recalled how they would don disguises to go on dates unnoticed. He described how they would dress up, him with a mustache and a hat with hair, and Madonna as an old lady, allowing them to enjoy their dates in relative anonymity.

However, their relationship wasn’t destined to last. Vanilla Ice revealed that part of the reason they split was due to Madonna’s desire to take their relationship to the next level, despite her lingering feelings for her ex, Sean Penn. He described Madonna as having a “desperate neediness” and an “impatience to get married.” He also shared that he felt Madonna still loved Penn, a fact she confirmed to him. Despite their breakup, Vanilla Ice spoke warmly of Madonna, describing her as a “sweetheart.”

10. Tupac Shakur

Tupac Shakur

Her romantic journey led her to another renowned rapper, Tupac Shakur, after actress Rosie Perez introduced them at the 1993 Soul Train Awards. However, their romance was short-lived. In a heartfelt letter written to Madonna in January 1995, Tupac explained why he ended their relationship. This letter was made public in 2017 when TMZ published a redacted version of it.

In the letter, Tupac expressed his concern about how their relationship would impact his image. He wrote, “For you to be seen with a Black man wouldn’t in any way jeopardize your career, if anything it would make you seem that much more open and exciting. 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. I never meant to hurt you.”

Tupac also addressed a comment Madonna allegedly made in an interview, saying, “I’m off to rehabilitate all the rappers & basketball players.” This statement hurt Tupac, as he had not known Madonna to be involved with any other rappers. He admitted that his response to her comment was a defensive reaction, driven by hurt and a desire to protect his heart and ego.

Throughout the letter, Tupac apologized to Madonna for not being more transparent about his feelings at the time of their breakup. He reflected on his growth, both spiritually and mentally, since their relationship ended. He wrote, “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.”

10. Dennis Rodman

Dennis Rodman

One of the “basketball players” Madonna was reportedly interested in rehabilitating was none other than Dennis Rodman. The two had a brief romance in 1994, and despite its short duration, Rodman had fond memories of their time together. In his 1996 memoir, “Bad as I Wanna Be,” he wrote, “We never had any problems. It was one of the easiest relationships I’d ever been in.”

According to Rodman, Madonna took their relationship quite seriously. In a September 2019 interview on The Breakfast Club, he made a surprising claim that Madonna had offered him $20 million to father her child. Although he claimed they attempted to conceive, Madonna and Rodman never had a child together.

11. John F. Kennedy Jr.

John F. Kennedy Junior and madonna

In the ’90s, Madonna reportedly had a flirtatious connection with John F. Kennedy Jr., although it seems their interaction was limited to playful faxes and phone calls.

A friend of JFK Jr. shared with PEOPLE that their flirtation was light-hearted and fun. JFK Jr. was particularly proud of having given Madonna the nickname ‘M,’ which he used when writing or faxing her. This was a time before cell phones, and he was quite territorial about having started that moniker for her.

The pair were attracted to each other, but their busy schedules made it difficult for them to spend time together. Madonna was on tour, and JFK Jr. was working. They managed to see each other a few times, and their interactions were characterized by friendly and flirty banter. However, their connection didn’t evolve into a full-fledged relationship. As the friend put it, “They had a flirty and friendly banter but it wasn’t a ‘relationship.'”

12. Carlos Leon

Carlos Leon

Romantic journey took an unexpected turn in 1994 when she happened to jog past personal trainer Carlos Leon in Central Park. Mistaking him for her ex, Jim Albright, she sent a member of her team to find out who he was. Once the misunderstanding was cleared up, Madonna and Leon quickly hit it off. However, Leon reportedly struggled with the intense media scrutiny that came with dating the famous singer.

At Madonna’s 37th birthday party in August 1995, the couple shared their plans to have a child together once Madonna finished filming “Evita.” To her surprise, Madonna discovered she was already 11 weeks pregnant during the filming. She was reportedly concerned about how her pregnancy might affect the production.

On October 14, 1996, Madonna gave birth to her first child with Leon, a daughter they named Lourdes “Lola” Maria Ciccone Leon. Despite their joy at becoming parents, Madonna and Leon decided to end their relationship in May 1997. Rosie O’Donnell, a close friend of Madonna’s, told biographer Andrew Morton that it was a genuine relationship and that they made a “valiant effort” to stay together.

Fortunately, their breakup was amicable. Madonna and Leon remained “good friends” and worked together to co-parent their daughter, Lourdes, maintaining a strong bond for the sake of their child.

13. Guy Ritchie

Madonna’s love life took a significant turn in 1999 when she met director Guy Ritchie at a party hosted by mutual friends Sting and Trudie Styler. Madonna was immediately smitten, describing a “premonition” of her life fast-forwarding and being taken by Ritchie’s confidence and risk-taking nature. Her friend Rupert Everett also approved of Ritchie, noting his hardworking nature.

However, Ritchie didn’t fall for Madonna instantly. Their relationship was on and off for several months. By January 2000, Madonna confessed to PEOPLE that she was in love with Ritchie, describing their romance as “excellent.” In March, the couple announced they were expecting a child together, and their son Rocco Ritchie was born on August 11, 2000.

On 42nd birthday, just six days after Rocco’s birth, Ritchie proposed to her with a ring hidden in a crumpled paper bag. The couple married on December 22, 2000, in a private ceremony at Skibo Castle near Dornoch, Scotland.

Despite their initial happiness, Madonna and Ritchie’s relationship faced numerous challenges, and they announced their divorce in October 2008. Insiders cited a range of issues, including Madonna’s alleged emotional affair with baseball player Alex Rodriguez, lifestyle differences, and Madonna’s devotion to Kabbalah and the spotlight, which Ritchie didn’t share.

In 2011, Ritchie reflected on their marriage in an interview with Details magazine, expressing no regrets and appreciating the children that came from it. However, the split wasn’t entirely amicable. Madonna and Ritchie had a bitter custody battle over Rocco that lasted from December 2015 until June 2016.

  • If you want to read more articles on Dating check here.

14. Alex Rodriguez

Alex Rodriguez

Before her divorce from Guy Ritchie was finalized, Madonna was rumored to be involved with Yankees player Alex Rodriguez. Rodriguez’s then-wife, Cynthia Scurtis, filed for divorce in September 2008, and her attorney accused Rodriguez of having an “affair of the heart” with Madonna, which allegedly led to their split.

In a statement before her own divorce announcement, Madonna denied any romantic involvement with Rodriguez. She told PEOPLE, “I know Alex Rodriguez through Guy Oseary, who manages both of us. I brought my kids to a Yankee game. I am not romantically involved in any way with Alex Rodriguez. I have nothing to do with the state of his marriage or what spiritual path he may choose to study.”

Despite insiders claiming that Madonna and Rodriguez shared a “spiritual, emotional and romantic bond,” Rodriguez maintained that he and she were just friends.

15. Brahim Zaibat

Brahim Zaibat

In September 2010, Madonna started dating French model and dancer Brahim Zaibat after he performed at the launch of her Macy’s clothing line, Material Girl. Their relationship lasted for three years, during which they enjoyed a trip to Paris and Zaibat performed during Madonna’s 2012 MDNA tour.

In a 2012 interview with OK! Magazine, Zaibat shared that he wasn’t intimidated by Madonna when they first met. He described her as “just a woman almost like the others,” albeit an exceptional artist and world-famous. He expressed happiness at meeting her and revealed that their initial connection was their shared love of dance. He also mentioned that their relationship was progressing naturally, without rushing.

The couple made a public appearance together at the 2013 Met Gala, but they parted ways in December of the same year. E! News reported that the split was due to their “busy and conflicting schedules.”

16. Timor Steffens

Timor Steffens

After parting ways with Brahim Zaibat, Madonna had a brief “fling” with choreographer Timor Steffens in 2014. According to E! News, they met in Switzerland through their mutual friend, designer Valentino Garavani.

Despite their relationship being short-lived, Steffens, who is 30 years younger than Madonna, was open about their romance. In an interview with The Mirror, he said, “There is an age gap between me and Madonna but I don’t notice it. My girlfriends have always been older than me and that’s how I like it. I learn a lot.”

Steffens admired Madonna’s individuality and strength, saying, “She always looks for new ­challenges in life. When everyone walks the right path, she will walk the left path to show that she has a vision and her own way of expressing. She is a very strong woman and doesn’t need to follow the mainstream. That’s what makes her an artist.”

Their relationship reportedly ended shortly after Steffens spoke to the tabloid.

17. Ahlamalik Williams

In June 2019, Madonna sparked rumors that she was dating dancer and choreographer Ahlamalik Williams, who is 36 years her junior. The speculation began when she posted a since-deleted Instagram video of them dancing together to celebrate her album Madame X topping the Billboard charts. The couple reportedly first met in 2015 when Williams was a dancer on her Rebel Heart tour.

Throughout their relationship, Madonna and Williams kept a relatively low profile, but he was a constant presence in her life and on her Instagram feed until 2021. They celebrated Thanksgiving together with her children and dressed up as elves with her family in December. They also celebrated Madonna’s 62nd and 63rd birthdays together. However, they reportedly ended their relationship in April 2022, after three years of dating.

18. Josh Popper

In early 2024, Madonna was spotted spending time with boxing trainer and “Summer House” star Josh Popper, leading to speculation that they might be dating. The two reportedly met when Popper was training Madonna’s son, David Banda, at Bredwinners gym in New York City, which Popper owns.

On February 12, 2024, Madonna appeared in photos posted by Popper on Instagram. In one image, the pop icon is seen posing with Popper and his coaches after he won a match at Gleason’s Gym. In another photo, the pair are seen together, with Madonna holding onto Popper’s arm.

Madonna was later seen attending another one of Popper’s boxing matches at the Classic Car Club in New York City on March 3. She shared photos from the event on her Instagram Story.

As of now, neither Madonna nor Popper have publicly commented on the nature of their relationship.

To Who Was She Married

Her first marriage was to Hollywood star Sean Penn. They met on the set of her “Material Girl” music video in 1985, and after a whirlwind romance of six months, they tied the knot. However, their marriage was marked by rumors of fights, infidelity, and jealousy. After four tumultuous years together, they decided to part ways in 1989.

Second marriage was to renowned filmmaker Guy Ritchie. They met in 1998 and fell in love. In August 2000, Madonna gave birth to their son, Rocco. The couple got married in December of the same year. In 2006, they expanded their family by adopting a child, David. However, their relationship didn’t last, and they divorced in 2008.

Also has a daughter, Lourdes Maria, with her former partner Carlos Leon. In total, Madonna is a mother to six children. She has one child each with Carlos Leon and Guy Ritchie. She adopted David Banda in 2006 and Mercy James in 2009. In 2017, she adopted twins Esther and Stella Mwale.


1. What is Madonna’s net worth?

As per celebrity net worth, Madonna has a net worth of $850 million.

2. What is the name of Madonna’s children?

Madonna has 6 kids. Their names are Lourde Maria Ciccone Leon, Rocco Ritchie, David Banda, Mercy James, Esther, and Stella Mwale.

3. What is Madonna’s age?

Madonna was born on 16 August 1958. As of 2022, she is 64 years old.

Final Words

From her early days in the spotlight to her current status as the undisputed Queen of Pop, Madonna’s love life has been as diverse and dynamic as her career. Her relationships, ranging from Hollywood stars like Sean Penn and Guy Ritchie to dancers like Ahlamalik Williams, have kept fans intrigued for decades.

Each relationship has been a chapter in Madonna’s life, contributing to her growth as an artist and a woman. Despite the ups and downs, Madonna’s romantic history is a testament to her resilience, her independence, and her unapologetic approach to life and love.

All Posts


Related Posts