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All About Madonna's Past Relationships; What You Need to Know About Her Dating History Amid Alleged New Romance With Akeem Morris
Madonna's relationships with various boyfriends, husbands, and rumored flings have kept her love life in the spotlight for years, mirroring her decades-long iconic career and ongoing search for love.
Madonna's personal life has often been in the spotlight, particularly her relationships and family. Early in her career, she had several high-profile romances with stars like Warren Beatty and Tupac Shakur. She also had a relationship with trainer Carlos Leon, with whom she welcomed her first child, Lourdes Leon, in 1996.
Madonna has been married twice. Her first marriage was to actor Sean Penn, lasting from 1985 to 1989. She later married filmmaker Guy Ritchie in 2000, with their marriage ending in divorce in 2008. Reflecting on her marriages in a 2022 YouTube Q&A, Madonna humorously noted that getting married both times" might not have been the best decision.
Currently, Madonna is in a relationship with Jamaican soccer player Akeem Morris. She went public with their relationship on Instagram in July 2024, shortly after her breakup with ex-boyfriend Josh Popper in May. Let's take a look back at Madonna's romantic relationships over the years.
Dan Gilroy
Madonna credits her ex-boyfriend Dan Gilroy with inspiring her shift from dance to music. In a 1984 interview with Rolling Stone, she recalled meeting Gilroy at a party in 1979. After spending a few nights with him at an abandoned synagogue in Queens, New York, where he lived with his brother, Gilroy introduced her to the guitar by tuning it to an open chord and showing her how to strum. This moment sparked a new passion in Madonna, prompting her to cut back on her dance classes and focus more on singing.
Not long after this, Madonna was invited to Paris to work as a background singer and dancer for Patrick Hernandez. While abroad, she felt lonely and disconnected, but the letters she exchanged with Gilroy provided comfort and kept her motivated. She described his letters as humorous and uplifting, often playfully reminding her of home and encouraging her to return.
Madonna's stint in Paris was cut short by a bout of pneumonia, forcing her to return to the United States. Back home, she reconnected with Gilroy, leading to a period of intense musical training that she fondly remembers as one of the happiest times of her life. She felt loved and supported by Gilroy, who was moved by her emotional songwriting.
During this time, Madonna began collaborating closely with Gilroy, eventually playing drums for his and his brother Ed's band, the Breakfast Club. As her involvement with the band deepened, she became more ambitious, eager to take on more prominent roles and learn everything she could about music. This drive to perform and sing more prominently in the band eventually caused tension between her, Gilroy, and his brother Ed. As a result, Madonna decided to leave both the band and her relationship with Gilroy to pursue her goal of becoming a singer full-time.
Reflecting on this period, Madonna acknowledged that her ambitious and commercially-minded approach differed significantly from Gilroy's. She was determined to learn everything she could to achieve her musical ambitions, demonstrating her early commitment to her career and the drive that would eventually make her a global pop icon.
Jean-Michel Basquiat
Madonna's relationship with artist Jean-Michel Basquiat in 1982 left a lasting impression on her, particularly his intense dedication to his craft. In a 2014 interview with Interview magazine, she recalled how Basquiat's passion for painting captivated her. She described moments when she would wake up in the middle of the night to find him not in bed but standing very close to a canvas, painting at 4 a.m. in a trance-like state. She was amazed by his commitment to his art, stating, "I was blown away by that, that he worked when he felt moved."
However, their relationship was brief, primarily due to Basquiat's struggles with addiction. During a March 2015 interview with Howard Stern, Madonna spoke candidly about their time together and his tragic battle with substance abuse, which ultimately led to his untimely death in August 1988 at the age of 27. Reflecting on their relationship, Madonna expressed admiration for Basquiat, calling him an amazing man and deeply talented. She also shared that when they broke up, Basquiat insisted she return all his paintings, which he then painted over in black.
Despite the end of their romantic relationship, Madonna's connection to Basquiat's art remained significant. She has introduced her children to his work, as noted in a now-deleted Instagram post referenced by W Magazine. This act indicates her enduring respect for Basquiat's artistry and his influence on her life.
John Benitez
Madonna's relationship with DJ John Benitez in 1983 marked a significant chapter in her early career. Benitez, who would later produce her hit song Holiday, quickly became more than just a professional collaborator; the two began dating and their romance was seen as serious by those around them. Friends of Benitez believed the couple was deeply in love, and there were even reports of an engagement and cohabitation.
Despite the strong connection, the relationship faced challenges. A notable rough patch occurred when Madonna reportedly had a fling with journalist Steve Neumann, who was dating her friend Erika Belle at the time. This incident strained her relationship with Benitez.
A friend of Benitez's reflected on their dynamic, telling PEOPLE, "He was in love with her. They were a great team. But she was the one in charge. She's a diva—man, they like to command attention." This characterization underscores Madonna's strong personality and determination to take control of her personal and professional life.
Ultimately, Benitez and Madonna's relationship ended in 1985, around the same time she met Sean Penn, who would later become her first husband. Despite the breakup, Benitez's contribution to Madonna's early music career, particularly through his production work, remains a notable part of her journey to stardom.
Sean Penn
Madonna and Sean Penn's relationship began in February 1985 when they met on the set of her Material Girl music video. The couple quickly developed a close bond and were married just six months later on Madonna's 27th birthday, which coincidentally fell the day before Penn's 25th birthday.
Madonna spoke highly of Penn during their early days together, noting their similarities. In July 1985, she stated, "We have so much in common that he's almost like my brother. His temperament is also similar to mine. That doesn't always make for ideal relationships, but I don't know what will happen." Their shared passion for their crafts led them to collaborate professionally, notably co-starring in the 1986 film Shanghai Surprise.
However, their marriage was fraught with challenges from the start. In April 1986, Penn's temper became evident when he assaulted songwriter David Wolinski, believing Wolinski was getting too close to Madonna. Penn was fined $1,000 and sentenced to a year of probation for the incident. According to a source close to Madonna, this was a pivotal moment for the singer: "The marriage had been undergoing stress all the time, but this was the first major stress, the first really traumatic episode for her. Wolinski was someone she knew, and it really shook her up."
Penn's volatile behavior continued to strain their marriage. Just months later, he had altercations with photographers in New York and became increasingly jealous of Madonna's professional relationships, particularly with model and singer Nick Kamen, who was working with Madonna on the track Each Time You Break My Heart. Despite Madonna's assurances, Penn was convinced they were having an affair.
The turmoil culminated on December 4, 1987, when Madonna filed for divorce, citing ongoing issues in their relationship. A representative for Madonna told PEOPLE, "There was no one direct incident leading up to this. 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." Although Madonna briefly reconsidered and withdrew her divorce filing, she ultimately decided to end the marriage for good in January 1989.
Despite their tumultuous past, Madonna and Penn have remained on good terms. In December 2016, during a charity auction, Madonna playfully declared she was still in love with Penn and even offered to remarry him if he bid $150,000, showing a sense of humor and lingering affection towards her former husband.
Tony Ward
In 1990, Madonna was romantically involved with model and actor Tony Ward, who appeared in her provocative Justify My Love music video. The video, known for its explicit content, was banned by MTV, which only added to its notoriety. Despite the intense chemistry between Madonna and Ward, their relationship was relatively brief.
The end of their romance coincided with a surprising revelation about Ward's personal life. According to a 1991 report by PEOPLE, Ward seemingly disappeared from Madonna's life around the same time that tabloids exposed his marriage to Amalia Papadimos, a 23-year-old woman he had previously dated. The couple had married in a spontaneous ceremony in Las Vegas on August 21, 1990, after Ward had already begun his relationship with Madonna. This revelation likely contributed to the abrupt conclusion of Madonna and Ward's relationship.
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Warren Beatty
Madonna and Warren Beatty's relationship began in 1990 after meeting on the set of Dick Tracy, where Beatty starred as the titular detective and Madonna played the sultry lounge singer Breathless Mahoney. Their romance lasted about 15 months, and despite the public's fascination with their pairing, their relationship was marked by disagreements, particularly regarding fame and publicity.
One notable point of contention arose during the filming of Madonna's documentary Truth or Dare. Beatty was initially reluctant to appear in the documentary, expressing his desire to stay out of it. Madonna, known for her strong will and dedication to her projects, responded with a rhetorical question about why she would include him. Eventually, Beatty agreed to be featured in the film on the condition that he would have approval over the footage used of him. Despite their efforts to navigate their differences, the relationship ended not long after Dick Tracy's release, largely due to their differing views on publicity and the pressures of fame.
Beatty later spoke highly of Madonna, describing her as a huge personality and praising her as a phenomenon in a 2016 interview with PEOPLE.
Michael Jackson
Madonna and Michael Jackson made headlines when they appeared together as a high-profile duo at the 1991 Academy Awards. However, their Oscars outing was reportedly more about spectacle than substance. Observers speculated that the pairing was a calculated move for publicity rather than a sign of a close personal relationship. While the two pop icons created a buzz on the red carpet, Madonna was said to have spent most of her time away from Jackson with her then-beau, Warren Beatty. The event was viewed by many as a strategic move to generate media attention, showcasing the power and influence of both Madonna and Jackson at the height of their careers.
Jim Albright
Jim Albright, who initially worked as Madonna's bodyguard, claimed in 2001 that their professional relationship evolved into a secret three-year affair starting in February 1991. According to Albright, their relationship deepened over time, despite Madonna's increasing distance after he ended his previous relationship to be with her. When he stepped down as her bodyguard in 1993, their bond reportedly grew even closer, with Albright stating that Madonna would speak to him every day.
Albright also alleged that Madonna was considering marriage but insisted on a prenup that he was unwilling to agree to. He described Madonna as becoming increasingly "insecure" and jealous, mentioning that she had affairs with various celebrities, including Ingrid Casares and comedian Sandra Bernhard. Albright's own infidelity was reportedly the final straw for Madonna, leading her to end their relationship.
Albright's account paints a picture of a tumultuous and complex relationship, marked by both emotional intensity and significant challenges, with Madonna's alleged infidelity and Albright's own actions contributing to the eventual breakup.
Vanilla Ice
Madonna and Vanilla Ice's relationship in 1991 was a notable chapter in both their lives, marked by their attempt to keep their romance under wraps. Vanilla Ice, who was nine years younger than Madonna, described their relationship as involving fun and creative efforts to maintain privacy. He recalled wearing disguises to go to movies and dinners, with Madonna sometimes dressing as an old lady to avoid recognition. Vanilla Ice appreciated these moments of normalcy away from the public eye.
Their relationship lasted about eight months before ending in 1992. Vanilla Ice attributed part of the breakup to Madonna's desire for a more serious commitment, which clashed with his own feelings and her lingering emotions for her ex-husband Sean Penn. In his interview and in Andrew Morton's book, Vanilla Ice noted that Madonna's lingering feelings for Penn created tension in their relationship, and he sensed a sense of desperation and neediness from her regarding marriage. Despite the end of their romance, Vanilla Ice described Madonna as a sweetheart and appreciated their time together.
Tupac Shakur
Tupac Shakur's letter to Madonna, written from prison in January 1995, provides a deep insight into his feelings about their short-lived relationship and his struggles with his public image. In the letter, Tupac reflects on the complexities of their romance and his own insecurities about their relationship.
He explains that he felt torn about being seen with Madonna, fearing it might negatively impact his image and alienate some of his supporters. Tupac acknowledges that his perception of the situation was influenced by his own fears and insecurities, and he expresses regret for not being more transparent with her during their time together.
Tupac's reference to Madonna's comment about rehabilitating all the rappers & basketball players reveals how deeply hurt he felt by the remark, interpreting it as a slight against their relationship. He admits that this pain led him to make hurtful comments in return, which he now regrets.
In closing, Tupac expresses his growth and maturity since their breakup, emphasizing that he has come to understand the situation better and regrets any pain he may have caused Madonna. His apology reflects a sense of self-awareness and acknowledgment of his past mistake
Dennis Rodman
Dennis Rodman's brief romance with Madonna in 1994 is indeed a notable part of his colorful past. In his memoir Bad as I Wanna Be, Rodman described their relationship as one of the most effortless he had experienced, despite its short duration.
Rodman's 2019 interview on The Breakfast Club added a provocative detail: he claimed that Madonna had offered him $20 million to get her pregnant. This claim, while intriguing, remains unverified beyond Rodman's own account. The relationship ended without resulting in a child, but the story of Madonna's alleged offer continues to fuel speculation and interest about their time together.
John F. Kennedy Jr.
The flirtation between Madonna and John F. Kennedy Jr. in the '90s was reportedly a playful and flirtatious exchange rather than a full-blown relationship. Their connection was marked by flirty phone calls, with JFK Jr. apparently taking credit for popularizing the nickname M for Madonna.
Their interactions, described as having a mix of charm and irreverence, were more about mutual attraction and teasing rather than developing into a serious relationship. The challenges of their busy schedules, Madonna’s tour commitments and JFK Jr.'s work, meant their flirtation remained largely a series of light-hearted exchanges rather than evolving into a deeper relationship.
Carlos Leon
Madonna and Carlos Leon's relationship began in 1994 after a serendipitous meeting in Central Park. Despite the initial mix-up with Madonna mistaking Leon for her former flame Jim Albright, the two quickly connected. Their relationship became serious, and by Madonna's 37th birthday party in August 1995, they announced their intention to have a child together after Madonna completed filming Evita.
Madonna's pregnancy came as a surprise during the filming, as she was 11 weeks along. She reportedly worried about how it would affect her work on the film. On October 14, 1996, Madonna gave birth to their daughter, Lourdes Lola Maria Ciccone Leon.
Though Madonna and Leon broke up in May 1997, the split was described as amicable. They maintained a good friendship and co-parented Lourdes effectively. Madonna's close friend Rosie O'Donnell noted that their relationship had been genuine and that they made a strong effort to stay together despite the challenges.
Guy Ritchie
Madonna and Guy Ritchie met at a party hosted by Sting and Trudie Styler in 1999, and their connection was immediate. Madonna was captivated by Ritchie's confidence and self-awareness, while Ritchie was initially hesitant, having an on-again, off-again relationship with her for several months. By early 2000, their relationship solidified, and they announced they were expecting a child together. Their son, Rocco Ritchie, was born on August 11, 2000.
Madonna and Ritchie married on December 22, 2000, at a remote location, Skibo Castle in Scotland, with a small group of close friends and family in attendance. Despite their initial enthusiasm for each other, their marriage faced challenges, including lifestyle differences and Madonna's rumored emotional affair with baseball player Alex Rodriguez. Their problems, which had been growing since around 2007, ultimately led to their separation and divorce announcement in October 2008.
The split was complicated by differences in their lifestyles, with Madonna's devotion to Kabbalah and public life clashing with Ritchie's more low-key approach. A source close to the couple noted that they were living separate lives and only came together for public appearances.
Ritchie later reflected on their marriage in a 2011 interview with Details magazine, acknowledging that while the marriage had its difficulties, he did not regret it and valued the positive aspects, particularly their children.
The aftermath of their divorce saw a contentious custody battle over Rocco, which lasted from December 2015 until June 2016.
Alex Rodriguez
When Alex Rodriguez and his then-wife Cynthia Scurtis divorced in September 2008, Scurtis' attorney accused Rodriguez of having a romantic affair with Madonna, leading to their split. In response to these allegations, Madonna clarified her position in a statement to 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 these denials, reports suggested that Madonna and Rodriguez had a spiritual, emotional, and romantic bond. Rodriguez, however, maintained that their relationship was purely platonic, framing it as a friendship.
Brahim Zaibat
Madonna's relationship with Brahim Zaibat, which began in September 2010, was marked by their shared passion for dance and a few high-profile appearances. Zaibat, who had performed at the launch of Madonna's Material Girl clothing line, also joined her on stage during her 2012 MDNA tour.
In January 2012, Zaibat told OK! Magazine that he wasn't intimidated by Madonna, describing her as just a woman almost like the others despite her fame. He highlighted their connection through dance and noted that their romance was progressing naturally.
The couple made a notable appearance together at the 2013 Met Gala. However, by December of that year, they had parted ways. E! News reported that their busy and conflicting schedules were a significant factor in their split.
Timor Steffens
After her split from Brahim Zaibat, Madonna had a brief romance with choreographer Timor Steffens in 2014. The two met in Switzerland through their mutual friend, designer Valentino Garavani. Despite their short-lived relationship, Steffens spoke positively about Madonna, noting that their age difference of 30 years didn’t affect him and that he preferred dating older women.
In an interview with The Mirror, Steffens praised Madonna for her nonconformity and strength, highlighting her desire to take unconventional paths and showcase her unique artistic vision. He admired her for not following mainstream trends, which he felt contributed to her artistic identity.
The romance ended shortly after Steffens' comments to the tabloid, with the split reportedly occurring not long after their brief fling.
Ahlamalik Williams
Madonna and Ahlamalik Williams began dating in June 2019, following a video Madonna posted on Instagram where they celebrated her album Madame X reaching the top of the Billboard charts. Williams, who is 36 years younger than Madonna, was introduced to her in 2015 when he danced on her Rebel Heart tour.
Throughout their relationship, which lasted until April 2022, Madonna and Williams kept their romance relatively private. Williams appeared frequently on Madonna's Instagram, and they spent significant time together, including celebrating Thanksgiving with her children and dressing as elves for the holidays. They also celebrated Madonna’s 62nd and 63rd birthdays together.
The couple split in April 2022 after three years together, marking the end of their low-key but affectionate relationship.
Josh Popper
In early 2023, Madonna and boxing trainer Josh Popper were spotted together, sparking speculation about a possible romance. They met when Popper was training Madonna's son David Banda at his gym, Bredwinners in NYC.
Photos of Madonna with Popper and his team appeared on Instagram in February 2023, including one where she was seen holding onto Popper's arm and another from a match at Gleason's Gym. Madonna also attended one of Popper's boxing matches at the Classic Car Club in NYC on March 3.
Their rumored relationship seemed to gain traction with a shared kiss on stage during Madonna's Celebration Tour stop in Brooklyn in December 2023. However, it's unclear when they officially ended their relationship in 2024.
Akeem Morris
Madonna and Akeem Morris first crossed paths during her Paper Magazine cover shoot in August 2022. Their relationship didn't make headlines until July 2024, when they were seen cozying up together in New York City on the Fourth of July.
By August 2024, Morris was seen with Madonna in Italy, celebrating her 66th birthday. Their public appearances together suggest a growing relationship.
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