MADONNA is one of the most successful and iconic performers in history, and has been making hits for over four decades.
The star, who suffered a health scare in June 2023 and is known as the Queen of Pop, has had several high profile relationships throughout the years, and is known for her big family.
Madonna’s relationship history
Dan Gilroy
Madonna dated screenwriter and film director Dan Gilroy in 1979.
Back then, Madonna was an aspiring dancer and she has credited Gilroy with igniting her passion for being a music artist.
Speaking about the pair’s relationship, Madonna, who was 21 when she met Dan, has described it as “one of the happiest times of [her] life”.
Jean-Michel Basquiat
Madonna dated the legendary late artist Jean-Michel Basquiat in 1982.
In 2014, she recalled to Interview magazine that the painter, who died of an accidental drug overdose when he was just 27, would often work in the middle of the night.
She said: “I remember getting up in the middle of the night and he wouldn’t be in bed lying next to me; he’d be standing, painting, at four in the morning, this close to the canvas, in a trance.
“I was blown away by that, that he worked when he felt moved.”
John Benitez
From 1983 to 1985 Madonna dated producer and DJ John “Jellybean” Benitez.
Benitez produced Madonna’s hit song Holiday.
Sean Penn
Madonna and actor Sean Penn met on the set of her Material Girl music video.
They began dating in February 1985 and married just six months after their first meeting.
The couple later co-starred in the 1986 film Shanghai Surprise.
Madonna filed from divorce from Penn in 1987 and later requested to withdraw it, but the pair divorced for good in 1989.
The stars have remained friendly since their romance ended.
Tony Ward
Madonna briefly dated model and actor Tony Ward after meeting him when he featured in her iconic 1990 Justify My Love music video.
Their romance was short-lived and they had split by 1991.
Warren Beatty
Madonna and legendary actor Warren Beatty dated for just over a year.
The pair met on the set of 1989 movie Dick Tracy but split not long after the film was released.
Vanilla Ice
Madonna began dating Ice Ice Baby star Vanilla Ice in 1991.
The duo split after eight months, and Vanilla Ice, real name Robert Matthew Van Winkle, has since revealed that they used to wear disguises when they went on dates so they wouldn’t get recognised.
Tupac Shakur
After meeting at the 1993 Soul Train Awards, Madonna and late rap legend Tupac Shakur dated.
Their romance, which ended in 1995, was kept a secret until 2015 when Madonna revealed they had been in a relationship.
Read Related Also: The Secret Signal King Charles Gives His Staffers When He Wants to Get Out of a Conversation, Revealed by Body Language Expert
Letters from Tupac to Madonna have since been uncovered by TMZ.
Dennis Rodman
NBA legend Dennis Rodman and Madonna had a brief, but highly publicised, relationship.
The famous duo were together in 1993 and even tried for a baby together but never had a child.
Carlos Leon
Madonna and personal trainer Carlos Leon met in 1994.
In 1996 they welcomed daughter Lourdes Maria Ciccone Leon.
The former couple split in 1997 but have stayed good friends.
Guy Ritchie
Madonna met director Guy Ritchie in 1999 after being introduced by mutual friends Sting and Trudie Styler.
They began dating and in March 2000 they announced they were expecting a child together.
Their son, Rocco Ritchie, was born in August 2000.
In December of that year, Madonna and Guy married at a castle in Scotland.
They announced they were getting divorced in October 2008.
In 2006, Madonna and Ritchie adopted baby David Banda from an orphanage in Malawi.
After settling her divorce from Ritchie, Madonna adopted Chifundo “Mercy” James as a single mother.
She would go on to adopt twins Stella and Estere, who were also born in Malawi, in 2017.
Jesus Luz
Madonna and Brazilian model Jesus Luz dated in from 2009 to 2010.
He later credited the superstar for “influencing his mindset”, saying she “inspired” him to be more open and accepting.
Brahim Zaibat
Madonna had a three-year-long relationship with French model and dancer Brahim Zaibat from 2010 to 2013.
The pair attended the 2013 Met Gala together but split later that year.
Ahlamalik Williams
Though Madonna never spoke publicly about her relationship with dancer Ahlamalik Williams, his father gave the singer his seal of approval.
Drue Williams defended the couple’s more-than-30-year age gap to TMZ, saying: “Love has no age.”
Madonna and Williams called off their three-year romance in 2022.
Josh Popper
As of 2023, Madonna has most recently been linked to boxer Josh Popper.
Reality TV fans may recognise Popper from a brief appearance on Bravo‘s Summer House.
He starred in an episode of the show’s seventh season.
