Inside Madonna's complicated love life: From two marriages to six children and MANY toyboys as the Queen of Pop causes a stir by hinting she's come out as gay
Madonna has been one America's leading sex symbols since she shot to fame in the 1980s.
The queen of pop, 64, has never been shy about her love life, and has attracted some big names over the years.
She has six children: daughter Lourdes Leon, 25, son Rocco Ritchie, 22, son David Banda, 17, daughter Mercy James, 16, and twin girls Stella and Estere, 10.
With two marriages and plenty of toyboys in her past, it's no surprise Madonna sent the internet wild on Sunday after playfully hinting she's gay while taking part in a new viral TikTok trend.
The Material Girl hitmaker shared a clip of herself in her bathroom, attempting to throw a pair of hot pink panties into the trashcan and missing entirely.
'If I miss, I’m gay!' the mom-of-six captioned the post, which amassed 1.3 million views in the first hour alone.
After her miss, the songstress gives the camera a pointed look before dramatically turning around, throwing her hand up in the air.
It's unclear whether the star was simply joking or actually making a statement about her sexuality.
MailOnline has taken a deep dive into the mother-of-six's complicated romantic history over her long career.
Jean-Michel Basquiat (1982 - 1983)
![Rising stars: Madonna and the late Jean-Michel Basquiat dated in the 1980s](https://i.dailymail.co.uk/1s/2022/10/10/13/63291445-11299477-Rising_stars_Madonna_and_the_late_Jean_Michel_Basquiat_dated_in_-a-38_1665406394068.jpg)
Rising stars: Madonna and the late Jean-Michel Basquiat dated in the 1980s
Madonna briefly dated the late painter Jean-Michel Basquiat when both were rising stars in New York City.
Jean-Michel, who tragically died in 1988 at the age of 27, went on to become a hugely successful artist.
However, the pair's romance didn't last long and Madonna revealed their break=up was pretty ugly.
Appearing on the Howard Stern Show, she said: 'He wouldn’t stop doing heroin. He was an amazing man and deeply talented, I loved him.
'When I broke up with him he made me give [the paintings he gave me] back to him. And then he painted over them black.'
Tony Ward (1990 - 1991)
![Early love: Tony Ward was Madonna's boyfriend in the beginning of the 1990s, as well as her muse](https://i.dailymail.co.uk/1s/2022/10/10/14/63306061-11299477-image-a-54_1665410088599.jpg)
Early love: Tony Ward was Madonna's boyfriend in the beginning of the 1990s, as well as her muse
Tony Ward was Madonna's boyfriend in the beginning of the 1990s, as well as her muse.
The male model appeared in some of her music videos as well as her controversial photography book in 1992, which she simply titled Sex.
According to People on April 15, 1991: 'Madonna and male model Tony Ward, 27, her last boyfriend of record and one of the objects of her desire in the "Justify" video, are no longer an item.
'It may be a coincidence, but he seems to have dropped from her arm at about the same time tabloids revealed that he had married an old flame, Greek-Australian photographer Amalia Papadimos, 23, in a quickie ceremony in Las Vegas on Aug. 21, 1990—after he had begun dating Madonna.'
Sean Penn (1985 - 1989)
![Rocky marriage: Madonna was married to Sean Penn from 1985 until 1989. The couple are pictured attending an AIDS benefit November 11, 1987 in Los Angeles](https://i.dailymail.co.uk/1s/2022/10/10/14/63291431-11299477-Rocky_marriage_Madonna_was_married_to_Sean_Penn_from_1985_until_-a-39_1665407980766.jpg)
Rocky marriage: Madonna was married to Sean Penn from 1985 until 1989. The couple are pictured attending an AIDS benefit November 11, 1987 in Los Angeles
The singer was famously married to actor Sean Penn, after the duo met on the set of her Material Girl music video in January 1985.
They married on Madonna's 27th birthday just seven months later and she dedicated her third studio album True Blue (1986) to him, referring to him in the liner notes as 'the coolest guy in the universe'.
Their often tumultuous relationship was marked by several incidents of Sean reacting unpredictably and violently.
Madonna filed for divorce in December 1987, but withdrew the papers two weeks later.
In January 1989, Madonna filed for divorce again and reportedly withdrew an assault complaint against Penn following an incident at their Malibu home during the New Year's weekend.
John F. Kennedy Jr. (1987)
![Mingling with the Kennedy's: During a separation from Penn, Madonna reportedly dated the late John F. Kennedy Jr. for six months; Pictured 1997 in Las Vegas](https://i.dailymail.co.uk/1s/2022/10/10/14/63291447-11299477-Mingling_with_the_Kennedy_s_During_a_separation_from_Penn_Madonn-a-40_1665408026895.jpg)
Mingling with the Kennedy's: During a separation from Penn, Madonna reportedly dated the late John F. Kennedy Jr. for six months; Pictured 1997 in Las Vegas
During a separation from Penn, Madonna reportedly dated the late John F. Kennedy Jr. for six months.
The romance with the political heir didn't last long, as his mother, Jackie Kennedy, was said to not approve of the controversial singer and Madonna also reportedly took issue with John's temper.
Madge and JFK gave each other nicknames — she would call him 'Johnny' or 'Kennedy' and he would later say he started the trend of referring to the pop goddess as just 'M.'
Warren Beatty (1991)
![Movie star romance: She then dated movie star Warren Beatty, after they co-starred in his comic book movie Dick Tracy (pictured June 24, 1990)](https://i.dailymail.co.uk/1s/2022/10/10/14/63291451-11299477-Movie_star_romance_She_then_dated_movie_star_Warren_Beatty_after-a-41_1665408084311.jpg)
Movie star romance: She then dated movie star Warren Beatty, after they co-starred in his comic book movie Dick Tracy (pictured June 24, 1990)
The singer dated movie star Warren Beatty after they co-starred in his comic book movie Dick Tracy, where she starred as singer Breathless Mahoney.
The two ended up splitting due to their conflicting views of living in the public eye.
Speaking to People in 2016, Warren said: 'When we were going [out] and she was making the documentary Truth of Dare, I said, "I don’t want to be in it." And she said, "Why would I want you in it?”'
But the actor eventually conceded: 'I said if I can have approval, I don’t want to inhibit you.'
Vanilla Ice (1992)
![Ice, Ice baby! Madonna dated Vanilla Ice for eight months before splitting in 1992](https://i.dailymail.co.uk/1s/2022/10/10/14/63291453-11299477-Ice_Ice_baby_Madonna_dated_Vanilla_Ice_for_eight_months_before_s-a-43_1665408084346.jpg)
Ice, Ice baby! Madonna dated Vanilla Ice for eight months before splitting in 1992
Madonna dated Vanilla Ice for eight months before splitting in 1992.
The Like A Virgin singer dated the Ice Ice Baby rapper when he was 23 and she was 32.
He reportedly broke up with the star after she published her infamous coffee table book called Sex, in which he was featured, saying he was 'hurt' to be part of it.
Vanilla Ice later claimed in an interview with Yahoo Entertainment that his ex proposed to him.
He said: 'She actually proposed to me. I was like, ‘I’m too young for that. I’m just getting going here, I’m just revving up — I’m sorry. But she was a sweetheart, and we had such a great time.'
Tupac Shakur (1994)
![In love with a rapper: Madonna dated late rapper Tupac Shakur in the ¿90s but they split up due to societal constraints; Pictured 1994 in New York](https://i.dailymail.co.uk/1s/2022/10/10/14/63291457-11299477-In_love_with_a_rapper_Madonna_dated_late_rapper_Tupac_Shakur_in_-a-44_1665408084354.jpg)
In love with a rapper: Madonna dated late rapper Tupac Shakur in the ’90s but they split up due to societal constraints; Pictured 1994 in New York
Madonna and the late rapper Tupac Shakur dated in the ’90s after Rosie Perez introduced them at the Soul Train Awards in 1993.
The duo reportedly split up due to societal constraints, with Tupac breaking up with the singer in a letter from prison a year before he was fatally shot.
Tupac told Madonna that he was uncomfortable with the image of dating a white woman because he 'would be letting down half of the people who made [him] what [he] thought [he] was'.
Dennis Rodman (1994)
![From rapper to baller: Following her romance with Tupac, the singer was briefly involved with former Chicago Bulls basketball star Dennis Rodman for two months](https://i.dailymail.co.uk/1s/2022/10/10/14/63291455-11299477-From_rapper_to_baller_Following_her_romance_with_Tupac_the_singe-a-45_1665408084357.jpg)
From rapper to baller: Following her romance with Tupac, the singer was briefly involved with former Chicago Bulls basketball star Dennis Rodman for two months
Following her romance with Tupac, the singer was briefly involved with former Chicago Bulls basketball star Dennis Rodman for two months.
Though only together for a short period of time, the athlete revealed Madonna wanted to have a child with him in his memoir, Bad As I Wanna Be.
He wrote: 'Madonna talked all the time about having a baby. I think she wanted every bit of Dennis Rodman—marriage, kids, everything.'
He recalled at one point while he was gambling in Vegas: 'I picked up the phone and Madonna was like, "I’m ovulating, I’m ovulating. Get your ass up here". So I left my chips on the table, flew five hours to New York and did my thing.'
He added: 'We got done and she was standing on her head in an attempt to promote conception—just like any girl trying to get pregnant. I flew back to Las Vegas and picked up my game where I left off.'
Carlos Leon (1995 - 1997)
![First baby: Madonna had her first child - daughter, Lourdes Leon, 25 - with personal trainer Carlos Leon, whom she dated for three years](https://i.dailymail.co.uk/1s/2022/10/10/14/63291961-11299477-First_baby_Madonna_had_her_first_child_daughter_Lourdes_Leon_25_-a-46_1665408084363.jpg)
First baby: Madonna had her first child - daughter, Lourdes Leon, 25 - with personal trainer Carlos Leon, whom she dated for three years
Despite not being able to have a child with Rodman, Madonna went on to get pregnant with personal trainer Carlos Leon, whom she dated for three years.
He caught her eye while they were both jogging in Central Park and the singer enlisted him as her trainer.
The two share a daughter, Lourdes Leon, 25, together and have maintained a good friendship.
Guy Ritchie (2000 - 2008)
![Married: She went on to marry director Guy Ritchie. The two were together for eight years and share son, Rocco, 22, and adopted son David Banda, 16 (Pictured in 2008)](https://i.dailymail.co.uk/1s/2022/10/10/15/63307297-11299477-Married_She_went_on_to_marry_director_Guy_Ritchie_The_two_were_t-m-71_1665411443280.jpg)
Married: She went on to marry director Guy Ritchie. The two were together for eight years and share son, Rocco, 22, and adopted son David Banda, 16 (Pictured in 2008)
One of Madonna's longest relationship is that with film director Guy Ritchie, whom she was married to for eight years.
The former couple reportedly met at the home of Trudie Styler (musician Sting‘s wife) in 1999 at a party.
They share son, Rocco, 22, and adopted son David Banda, 16, together.
They ended up divorcing over irreconcilable differences in 2008, with the split costing Madonna an eye-watering $92 million in what became one of the biggest divorce settlements ever.
Jesus Luz (2008 - 2010)
![String of boy toys: After her divorce was finalized, the star began dating 24-year-old Brazilian model Jesus Luz (pictured 2009)](https://i.dailymail.co.uk/1s/2022/10/10/14/63291427-11299477-String_of_boy_toys_After_her_divorce_was_finalized_the_star_bega-a-49_1665409749434.jpg)
String of boy toys: After her divorce was finalized, the star began dating 24-year-old Brazilian model Jesus Luz (pictured 2009)
Shortly after her divorce was finalized, the star began dating Brazilian model Jesus Luz.
The former couple met at a W magazine photoshoot in December 2008, and his career as a fashion model took off due thanks to his association with Madonna.
But his mother, who is 14 years younger than the Material Girl singer, did not approve of the relationship.
The 24-year-old was 28 years younger than Madonna, and they eventually split up due to not having many interests in common and their busy work schedules.
Brahim Zaibat (2010 - 2013)
![A love for younger men: Joining the list of younger models and dancers the star dated is Brahim Zaibat - a French dancer - who was 24-years-old at the time (Pictured 2013)](https://i.dailymail.co.uk/1s/2022/10/10/14/63291423-11299477-A_love_for_younger_men_Joining_the_list_of_younger_models_and_da-a-50_1665409749441.jpg)
A love for younger men: Joining the list of younger models and dancers the star dated is Brahim Zaibat - a French dancer - who was 24-years-old at the time (Pictured 2013)
Joining the list of younger models and dancers the star dated is Brahim Zaibat - a French dancer and choreographer - who was 24-years-old at the time.
He went on the MDNA world tour with her in 2012 and the duo also showed up together to the 2013 Met Gala, where they made a fashionable pair in punk inspired outfits.
Their romance, however, 'ran its course' as they split in December 2013, a source told Us Weekly.
'They were dancing and working together all the time, and they barely saw each other,' the insider added at the time.
Ahlamalik Williams (2018 - 2022)
![Recent romance: Madonna began dating her 28-year-old backup dancer, Ahlamalik Williams - who was almost 40 years her junior - in 2018; Pictured 2021](https://i.dailymail.co.uk/1s/2022/10/10/15/63291437-11299477-Recent_romance_Madonna_began_dating_her_28_year_old_backup_dance-a-69_1665411090971.jpg)
Recent romance: Madonna began dating her 28-year-old backup dancer, Ahlamalik Williams - who was almost 40 years her junior - in 2018; Pictured 2021
Madonna began dating her 28-year-old backup dancer, Ahlamalik Williams - who was almost 40 years her junior - in 2018.
Ahlamalik had first met Madonna when he auditioned for her Rebel Heart Tour back in 2015 as a backup dancer.
After landing the gig, he began working with the singer during her Madame X Tour in 2019 and 2020.
The pair called it quits after four years of dating in the spring of 2022.
Andrew Darnell (2022 - present)
![New romance? Madonna is currently rumored to be dating 23-year-old model Andrew Darnell](https://i.dailymail.co.uk/1s/2022/10/10/14/63291973-11299477-New_romance_Madonna_is_currently_rumored_to_be_dating_23_year_ol-a-52_1665410022368.jpg)
New romance? Madonna is currently rumored to be dating 23-year-old model Andrew Darnell
Madonna is currently rumored to be dating 23-year-old model Andrew Darnell.
The couple were first pictured kissing on the cover of Paper magazine in August of this year.
They were most recently spotted 'snuggling and cuddling' in September at musician REMA’s concert in NYC.
Madonna shared photos from their night out to Instagram, including one of Andrew with his arm wrapped around her as they snapped a selfie.
He was also present for her twin daughters Estere and Stelle's 10th birthday celebrations on where they toasted a drink for her Instagram Story.
Most watched News videos
- Putin's prized £228m supersonic nuclear bomber crashes and explodes
- Rioter attempts to smash police van window leaving officer 'trapped'
- Horrifying moment woman snatches pet dog from owner's front garden
- Horrifying moment thug attacks man with scooter in London
- Family of Hannah Jacobs call for greater awareness about allergies
- 'It worries me': Harry slams Elon Musk's spread of disinformation
- Nick Pisa updates on day one of Harry and Meghan's Colombia tour
- Dramatic moment Ukraine destroys Russian bridge in Kursk region
- Sickening moment Russian soldier displays Ukrainian severed head
- Tourists watch in shock as migrants get off boat on a Balearic beach
- Shocking moment a Russian strategic bomber crashes in Siberia
- 'What kind of creature are you?': Angry man destroys flower bed