HomeEntertainmentMadonna Dating History: Let's Spill Tea About Her Romances So Far

Madonna Dating History: Let’s Spill Tea About Her Romances So Far

Madonna has been always in the news for her edgy style and music. Soon after “Borderline” was her first Top Ten success in 1984, Madonna changed the course of mainstream music. Her music’s innovative fusion of post-disco dance and bubbly pop was a trick that quickly became her trademark.

Madonna carried underground sounds into popular culture over the course of a long career, focusing on dance club trends. It’s hardly surprising that the pop queen herself has captivated several prominent people and dated them. Madonna continues stealing the hearts of people. This list includes each man or woman that Madonna has ever been romantically involved with.

Dan Gilroy (1979 – 1981)

Dan Gilroy, a singer, and Madonna allegedly started dating in 1979 and broke up in 1981.

Sean Penn (1985 – 1989)

This two-time Oscar Award winner’s first wife was Madonna. The couple wed in August of the same year in a beautiful Maui ceremony following six months of dating. However, they were only married from 1985 until 1989.

Sean Penn revealed in a Late Show interview featuring Stephen Colbert that he is still in love with his ex after 30 years, irrespective of the fact that their marriage was dogged by controversy.

Lenny Kravitz (1990)

Lenny Kravitz with Madonna has been occasionally musical partners, most memorably in the song “Justify My Love,” but they were also said to have been in a relationship back in 1990. The two allegedly started falling for one another while they were recording.

Tony Ward (early 1990s)

Madonna’s partner and muse in the early 1990s was the model Tony Ward. He not only made appearances in a lot of her music videos, but he also appeared in her hotly contested coffee table picture book, Sex. Among many others, Ward was also shown in sexy pictures.

Vanilla Ice (1991)

One of Madonna’s most contentious relationships to this time may have been her romance with the rapper in the year 1991. Both supporters and opponents of these stars viewed this pair as a publicity gimmick.

Tupac Shakur (1993 – 1995)

Tupac Shakur was indeed an established American rapper, singer, and actor. According to statistics from 2010 he was among the best-selling musicians in the world, selling more than 75 million records globally.

The legendary rapper Tupac Shakur is regarded as one of the best musicians ever. His lyrics were mostly influenced by the East-West hip-hop war, societal issues, racism, violence, and challenges in inner cities.

After Rosie Perez linked them at the 1993 Soul Train Awards, Madonna began a relationship with the legendary late rapper Tupac Shakur, which is probably the most unexpected and frequently overlooked addition to the list.

Pac ended things with Madonna in something like a 1995 letter while he was incarcerated, as was revealed in a portion of the letter that was made public by TMZ.

Dennis Rodman (1994)

Dennis Rodman chased Madonna in 1993 as just a San Antonio Spur before chasing championships with Michael Jordan like a Chicago Bull.

Rodman dumped Madonna because she wanted to become pregnant with his child, as was explained in the 2019 ESPN program.

Carlos Leon (1994 – 1997)

Carlos Leon was among Madonna’s biggest loves, despite the fact that few people will remember his name.

Only lasting from 1995 to 1997, their union resulted in the birth of Lourdes Leon before they realized they would be better off being best friends rather than lovers.

Guy Ritchie (1998 – 2008)

2 years prior Guy Ritchie directed Madonna in Swept Away, and later Madonna wed the Gentleman filmmaker in the year 2000. In August 2000, she delivered the birth of their son Rocco, and in December of the same year, she and Guy married in Scotland. David was adopted by them in 2006, and they later got divorced in 2008.

In the end, they divorced in 2008 due to irreconcilable disagreements. One of the largest divorce settlements in history cost Madonna a shocking $92 million as a result of their breakup.

Jesus Luz (2008 – 2010)

The Brazilian model and the “Vogue” pop singer allegedly dated one another from 2008 till 2010, when they broke up.

Alex Rodriguez (2008)

In the summertime of 2008, Alex Rodriguez was supposedly linked to Madonna.

The former MLB star later dated (and was hitched to) Jennifer Lopez after moving on from Madonna.

Brahim Zaibat (2010 – 2013)

Madonna met Brahim Zaibat for the first time in the year 2010. From then, chemistry bloomed, leading to a relationship with the significantly younger guy that lasted until 2013.

Timor Steffens (2014)

In the guise of a fitness trainer called Timor Steffens, Madonna found herself yet another young guy in 2014. At the height of that summertime, their relationship was made public, but by the end of August, there were rumors that they had split up while on vacation.

David Blaine (2016)

David Blaine was another improbable and unexpected choice of companion for Madonna. He assisted her in 2016 in making amends with their estranged son Rocco, even though they ultimately decided to remain friends rather than continue their relationship.

Ahlamalik Williams (2019-2022)

From 2019 to 2022, Madonna dated Ahlamalik Williams, a quite younger man. Madonna and Ahlamalik “amicably” parted in early 2022. Ahlamalik Williams, a singer and dancer who was born in 1994, is a member of the RAW By Nature collective, which promotes urban performance art.

Andrew Darnell (2022)

Madonna was rumored to have dated 23-year-old model Andrew Darnell in late 2022. Andrew is represented by the international modeling agency IMG Models. While modeling appears to be Andrew’s main line of work, he has dabbled in television. In six parts of the famous HBOMax program called Betty, he made an appearance. He portrayed Sylvester in the television show.

According to sources, Madge is “living the best life” as well as “does not appear to care whatsoever” about the age of her new boyfriend, according to Hollywood Life. The romance doesn’t appear to have been confirmed by Madonna, though.


We have gone through the entire detailed history of Madonna’s romances. Though her status is yet unconfirmed, one can still see her with the latest man Andrew Darnell sometimes. It’s tough to comment about her getting married in future as there seems no indication of that. However, one can truly believe that pop star Madonna is living her life to the fullest!

Hi! I am a content writer and a copywriter from India. I can write in multiple niches and deliver work within deadlines.


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