Madonna's Impressive Dating Resume: From Artist To President

Madonna has been in the spotlight not only for her fantastic run as a music legend but also for her romantic relationships.

She's been linked to a number of high-profile partners over the years, including Dennis Rodman, Warren Beatty, and the late Tupac among others. After publicly being with men for most of her life, Madonna threw fans into a tizzy in October 2022 when she created a TikTok video that seemed to hint at her coming out as gay. That’s as far as the latest details on her sexuality go as she hasn't discussed her sexuality directly.

As her Celebration Tour is set to take the world by storm, let’s take a look at everyone Madonna’s dated throughout her storied career.

Madonna had a short-lived relationship with artist Jean-Michel Basquiat in 1982. She admired his dedication to painting but noted that their relationship ended because of Basquiat's struggles with addiction. Tragically, Basquiat passed away in August 1988 at the age of 27 due to his battle with addiction.

Shortly after Gilroy and Madonna met at a party in 1979, they kicked off a romantic relationship. Within months, the “Ray of Light” singer, who was an inspiring dancer at the time, became a frequent face at the synagogue where Gilroy lived with his brother, Ed Gilroy, in Corona, Queens. 

During their time together, Dan and Madonna worked together for approximately a year, during which she became the drummer for their band, the Breakfast Club. Her strong desire to sing in the band led to tension between her and Dan, and it also strained the relationship between the Gilroy brothers. In the end, she chose to leave the band and her relationship with Dan so that she could fully pursue her singing career.

Madonna and Sean began dating in February 1985 after meeting on the set of her famous "Material Girl" music video. They got married on the “Like a Prayer” singer’s 27th birthday in a scenic wedding ceremony in Maui, just six months after they first met. Their marriage was marked by turbulence, with early signs appearing in April 1986 when Sean attacked songwriter David Wolinski for speaking to his wife. 

Affer a few yearshe “4 Minutes” performer eventually gave in to the challenges, and filed for divorce on December 4, 1987, which she reportedly requested to withdraw less than two weeks later

However, the pop star put her foot down and re-filed for divorce in January 1989. Madonna and Sean have since remained friendly, and in December 2016, the artist confessed she was "still in love" with her ex-husband, even offering to remarry him if he bid $150,000 in a charity auction.

In 1983, Madonna began dating DJ John "Jellybean" Benitez, who eventually produced her 1983 song "Holiday." They initially had a strong connection and even reportedly got engaged and moved in together. However, their relationship faced turbulence when the Grammy Award winner allegedly became involved with journalist Steve Neumann, who was in a relationship with her friend, Erika Belle. Their romance came to an end in 1985, around the same time Madonna met Sean Penn.

Madonna's involvement with the boxer became noticeable through photos shared by him on Instagram on February 12, 2023. One picture shows the pop star alongside the boxer and his coaches after he won a match at Gleason's Gym.

The speculations began even more intense after the "Dangerous Game" star showed — shared images of — her support by attending another one of Josh's boxing matches on March 3. As of now, neither Madonna nor Josh has made any public statements regarding their rumored relationship.

Madonna began dating the rapper Vanilla Ice in 1991, and their relationship ended after eight months. In an October 2021 interview, Vanilla claimed that his former flame had actually proposed to him during their relationship. He mentioned that he felt he was too young for marriage at the time and wasn't ready for it, even though he found Madonna to be a sweetheart, and they had a great time together.

The singer and the director met in 1999, and kicked off a romantic — albeit on-again-off-again — relationship. In March 2000, they announced they were expecting their first child together and their son, Rocco Ritchie, was born on August 11, 2000. The couple eventually got married on December 22, 2000, in a private ceremony at Skibo Castle in Scotland. Despite their initial attraction, their marriage faced difficulties, leading to their announcement of divorce in October 2008.

Madonna and Warren met while working together on the film “Dick Tracy” in 1989, and they dated for approximately 15 months starting in 1990. During their relationship, they initially disagreed about Beatty appearing in the documentary “Madonna: Truth or Dare.”

Ultimately, Warren agreed to be in the documentary but with conditions that allowed him approval over the footage used. Unfortunately, their relationship crumbled after the release of “Dick Tracy,” primarily due to their differences regarding public exposure and fame.

While Madonna's relationship with her former bodyguard had its ups and downs, the duo grew closer when Jim left his position as her security guard in 1993. In fact, the only reason they didn't exchange vows, even though they considered marriage, was because of Madonna's insistence on a prenup.

As their romance wound down, Jim claimed that his then-girlfriend had cheated on him with other celebrities, including Sandra Bernhard and Ingrid Casares. Despite the renowned songwriter's alleged infidelity, it was reportedly Jim's admission of being with someone else that led to the end of their relationship.

Madonna briefly dated the famous rapper after an introduction by actress Rosie Perez at the 1993 Soul Train Awards. However, their romance was short-lived, with the late Tupac explaining the reasons for ending the relationship in a letter to the singer written in January 1995. 

Madonna briefly dated Dennis in 1994. Even though their relationship was short-lived, Dennis wrote about it fondly in his 1996 memoir, "Bad as I Wanna Be."

Madonna crossed paths with personal trainer Carlos Leon in 1994 when she jogged past him in Central Park. Despite Carlos' reported struggle with the media attention that came with dating the iconic singer, the twosome became romantically involved.

The couple welcomed their first and only child together, daughter Lourdes "Lola" Maria Ciccone Leon, on October 14, 1996. Sadly, their relationship ended in May 1997.

Madonna started dating the French dancer and model in September 2010, and they had a three-year relationship. During that time, they shared moments like a trip to Paris and his performance during her 2012 MDNA tour. They even appeared together on the red carpet at the 2013 Met Gala. However, their relationship ended in December 2013, with "busy schedules" cited as a reason for the split.

After her split from Brahim, Madonna had a short "fling" with Timor in 2014. The choreographer, who is significantly younger than the Maverick founder, openly discussed their relationship with The Mirror. However, their romance didn't last long, and they reportedly broke up not long after Timor spoke to the outlet.

Madonna's relationship with the dancer and choreographer, who is 36 years her junior, first garnered attention in June 2019. This happened when she posted a now-deleted Instagram video of them dancing to celebrate her album, "Madame X,"topping the Billboard charts. 

While the Guinness World Records holder and Ahlamalik maintained a relatively discreet relationship, he was a notable presence in her life and featured in her Instagram posts until 2021. Reports indicate they parted ways in April 2022 after being together for three years.

Madonna was rumored to have had a flirtatious interaction with John during the 1990s, with them engaging in playful and irreverent conversations through faxes and phone calls. Although they made attempts to meet up a few times, their busy schedules and distance posed challenges, so their relationship remained on a flirty and friendly level without developing into a full-fledged romance.

In 1990, the New York City native briefly dated actor and model Tony Ward, who appeared alongside her in the "Justify My Love" music video. PEOPLE reported that in 1991 Tony seemed to have parted ways with Madonna around the same time that he had married an old flame, Amalia Papadimos, in a hasty Las Vegas ceremony on August 21, 1990. He was still dating the "Who's That Girl" actress at the time.