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Madonna is a woman who knows exactly what she likes…and what she likes is younger men.
“I have lovers who are three decades younger than me,” Madonna tells Harpers Bazaar in a new interview. “This makes people very uncomfortable. I feel like everything I do makes people very uncomfortable.”
But the 58-year-old cougar is totally comfortable in the bed of young hunks like Timor Steffens, who is nearly 30 years younger than her.
Here are five of Madonna’s noteworthy past lovers and some details about where they’ve been since their days dating the sexy star.
Timor Steffens was 26-years-old when he dated Madonna, who was nearly three decades his senior. The two broke up after a couple months of dating in 2014 because, as a source close to the singing superstar told Us Weekly, “It was never that serious.”
While Madonna was having a little fun with Steffens and focusing on her album “Rebel Heart,” Steffens admitted to learning a lot from the pop icon. “My girlfriends have always been older than me and that’s how I like it. I learned a lot,” he told the Daily Mail. “[Madonna] is a “big inspiration…She is a fighter, a strong independent woman.”
Since being Madonna’s arm candy, Steffens has pursued his passion for dancing. Currently, he is set to be a judge on “Dance Dance Dance,” a new show on Britain’s ITV network where celebrities learn and perform famous pop video and movie dance routines. This seems a perfect role for him, considering he’s choreographed for Usher and Michael Jackson. Steffens even appeared in Michael Jackson’s “This Is It” documentary.
Actor and activist Sean Penn, who is only two years younger than Madonna, was married to her for a little over four years in the ’80s. And though their relationship ended over two decades ago, Madonna admitted during her 2016 charity gala at Art Basel in New York that she’d marry him again. “I’m still in love with you,” the pop icon told him onstage.
To help her raise money for Malawi, Penn not only bid on several pricey items in the auction, he also handcuffed Madonna and crawled through her legs to coerce the crowd into placing higher bids. As a result, the black and white photos from her and Penn’s wedding were sold for $230,000.
The 56-year-old actor was last on screen in 2015’s “The Gunman” and has been focusing much of his attention lately on charity work. On Jan. 7, he hosted a fundraising gala in Beverly Hills, California and raised $37 million for the J/P Haitian Relief Organization.
He’s also been spotted taking a page out of Madonna’s dating playbook. Sean Penn was recently snapped getting steamy on an Hawaiian beach with Leila George, “Law and Order” actor Vincent D’onofrio’s 24-year-old daughter. At 56 years old, he’s just one year younger than George’s dad.
Madonna is three years older than former NBA star Dennis Rodman and although their ’90s fling lasted for only two months it had a big impact. And though it wasn’t very long, Madonna has said that she wanted Rodman to father her children. In his autobiography titled “I Should Be Dead By Now,” Rodman revealed that Madonna once gave him a “somebody died” type of call to tell him, “I’m ovulating, I’m ovulating. Get your ass up here.”
After that relationship ended, Rodman went on to date Vivaca A. Fox and Carmen Electra, retired from basketball, made a headline hitting trip to North Korea and has kept busy participating in a chicken wing eating contest.
Madonna and English filmmaker Guy Ritchie were married for seven and a half years before calling it quits in 2008. The superstar was ten years his senior, but she said their relationship felt more like a prison than a marriage. “There were times when I felt incarcerated. I wasn’t really allowed to be myself,” Madonna said to The Sun UK. A movie they made together, “Swept Awaty,” was slammed by critics and rejected by audiences.
Since the split, Ritchie has remained in London with their son Rocco – after winning an eight-month long custody battle against Madonna – and continues working on films. Though the English director has made a name for himself in crime pictures like “Lock, Stock and Two Smoking Barrels” and “Snatch,” he’s now venturing into the science fiction realm to direct “Cascade,” a movie about time travel.
“Ice Ice Baby” rapper Vanilla Ice was 24 and Madonna was 34 when the two had their eight-month fling in the ’90s. According to Vanilla Ice, he ended the relationship after the release of Madonna’s “Sex,” a coffee-table book of racy photographs. He told Digital Spy that he didn’t want to be in a “slutty package,” but he did admit that being with her was quite the experience since she was “older [and] a great lover.”
madonna and vanilla ice pic.twitter.com/wmI8Nyyfy1
— “hacking defense” (@gasnerpants) August 12, 2016
Madonna, on the other hand, isn’t as big a fan. She’s said that she’d rather be trapped on a desert island with Dennis Rodman than Vanilla Ice. “[Rodman] has a better sense of humor. Plus, he could always wear my clothes,” she said to Us Weekly.
Since dating Madonna, Vanilla Ice married Laura Giaritta in 1997 and focused on his showbiz career. He took a break from music to act in Netflix movie “The Ridiculous Six,” a western comedy where he played Mark Twain. He also appeared last year on “Dancing With the Stars,” where he lost, and is scheduled to be part of the I Love the 90s tour until Oct. 2017.