Everything to Know About Madonna's Exciting Love Life

Mon Jul 03 2023
By   tashi

Inside Madonna's thriving love life: The Queen of Pop boasts a long and active dating career!  

Popularly known as the Queen of Pop, Madonna, 64, has been a fixture in the music industry for as long as fans can remember. Madonna is a figure bigger than her illustrious career, her magnificent journey, and her stretching relevance in the modern entertainment industry.  

Known and loved for her evergreen hits like Like a Virgin, True Blue, Vogue, Frozen, and Take a Bow, Madonna has been relentless and blunt in her pursuit of self-expression and freedom. The multiple Grammy winner recently released her controversial 2003 American Life MV, once again bringing attention to her devil-might-care attitude.  

Inside Madonna's Long Romantic History!  

Madonna's dating stint over the years has been as versatile and aboveboard as her career. The Queen of Pop likes to keep it open and honest. Madonna's star-studded dating history truly resonates with her level of celebrity. The Like a Virgin hitmaker had her earliest dating experience with musician Dan Gilroy, who she credits for being an excellent influence on her.   

Madonna is known as the queen of pop.
Madonna boasts a long and active dating history. Photo Source: Instagram

"He was my saving grace," Madonna says of her ex, with whom she collaborated and learned extensively during her formative career. The pair's romance started in 1979 and had fizzled out by 1981. The Grammy winner's next muse would be artist Jean-Michel Basquiat.  

Madonna fondly recalls her brief romance with the artist, whose work ethic and passion left an abiding impression on her. "He was an amazing man and deeply talented. I loved him," Madonna said. The pop queen started a rather serious relationship with DJ John "Jellybean" Benitez after her split from Basquiat.   

Madonna has been married twice.
The Queen of Pop has been married and divorced twice. Photo Source: Instagram

She and John were even engaged at a point before Madonna decided it wasn't working anymore. The True Blue crooner's most notable relationship was with Oscar winner Sean Penn. Madonna and Penn met on the sets of her Material Girl mv and quickly fell in love. The romance quickly developed into a marriage, with the couple tying the knot the same year they started dating in 1985.  

The couple's four-year-short marriage was a tumultuous experience for the singer. Mostly because of Penn's toxic behavior. The actor would often embroiled in scuffles with anyone getting close to Madonna. Penn one time attacked songwriter David Wolinski for acting too friendly with the singer. Madonna's first marriage ended in 1989.   

Madonna was married to Sean Penn.
Madonna was once linked with Michael Jackson. Photo Source: Instagram

But the first failed nuptial didn't stop the Grammy winner from moving on in her love life. She soon started dating model Tony Ward in 1990, the same year she romanced the A-list philanderer Warren Beatty. The duo met on the sets of their flick Dick Tracy, and a romance ensued shortly after. Madonna was even linked with the late legend Michael Jackson at one point.  

Madonna's 90s flames unveil mostly short-lived romances with her bodyguard Jim Albright, Vanilla Ice, basketball player Dennis Rodman, and even Tupac Shakur, who broke Madonna's heart by breaking up with her via a letter he wrote from prison. The Like a Virgin crooner welcomed her first child, Leon, with personal trainer, Carlos Leon, who she dated from 1994 to 1997. 

Madonna is a mother to six.
The 'Material Girl crooner was married to Guy Ritchie for eight years. Photo Source: Instagram

The singer-turned-actress was head over heels for director Guy Ritchie, who swopped the pop queen right off of her feet with his fitting confidence and charm. The pair were on-and-off in the beginning but by 2000, it was a sealed deal. They welcomed their son, Rocco, in August 2000, and walked down the aisle in December.  

Initially enamored by each others' differences, Madonna and Richie soon found that they had very little in common. An insider claimed the duo lost their connection and problems got severe amid Madonna's alleged emotional affair with Alex Rodriguez. The couple finalized their divorce in 2008.  

The Vogue crooner's quest for love continued with model Jesus Luz, who she dated immediately after her second divorce. Madonna romanced dancer Brahim Zaibat for two years. The Material Girl hitmaker has since garnered a reputation for collecting boy toys. Madonna has dated staggeringly young boys like Timor Steffens, Ahlamalik Williams, and more.   

Who is Madonna Dating?   

The queen of pop was recently rushed to hospital amid a health scare. Madonna reportedly suffered a serious bacterial infection and is now feeling better after intensive care. The singer isn't navigating this tough time alone as she had her young beau, Josh Popper, right beside her.   

Madonna shares adopted four of her six kids.
The singer was recently rushed to hospital due to a health scare. Photo Source: Instagram

Popper, 29, a boxer coach, posted an inspirational quote ahead of Madonna's world tour, and amid her health scare. "Give yourself permission to live a big life. Step into who you were meant to be. Stop playing small. You are meant for greater things," the boxer wrote. Madonna's new romance with Josh is being chalked as her one more fling with a boy toy.  

The singer had dated 23-year-old model Andrew Darnell before Popper. But unlike her previous younger boyfriends, Madonna hinted at things being a little more serious with Popper as she debuted the boxer on her Instagram. Sharing a picture of herself clinging onto Josh's big arm, Madonna wrote, "In a male-driven culture, there are always exceptions."    

Madonna, 64, is dating Josh Popper, 29! 

Madonna's latest flame, Popper, is reportedly training one of the singer's six kids at Flatiron District gym Bredwinners, the website of which describes Josh as "a lifelong athlete and a full-time coach." Aside from her two kids with her previous partners, Madonna has four adopted kids, David, 18, Mercy, 17, and twins Stella and Estere, 10.  

Stay connected to Married Celeb for more.

Latest Posts