What Madonna Has To Say About Dating Younger Men

When it comes to love and relationships, Madonna has never been one to hold back, especially while in public. She had two very high-profiled marriages to actor Sean Penn and director Guy Ritchie. In an interview with Esquire back in 2009, Ritchie made his thoughts clear about his ex-wife. "She's a manifester, if there ever was one. First-rate manifester. Madonna makes things happen," he shared. "Put Madonna up against any twenty-three-year-old, she'll outwork them, outdance them, outperform them. The woman is broad. And, of course, here you go: I still love her."

And while there's no doubt that Madonna has had her fair share of ups and downs in her marriages and her relationships, a lot of her fans can't help but notice that she's started her own trend of dating men that are clearly not in the same age bracket as her. In fact, she hasn't dated a guy anywhere near in age to Ritchie (who is almost exactly ten years her junior) since their divorce in 2008. And what Madonna has to say about dating men that are much younger than her has certainly surprised her fans, seeing how she's often the picture of the utmost self-confidence and control. 

Madonna's still very aware of her shock factor

Madonna has been dating her boyfriend Ahlamalik Williams since 2019. The dancer was born the same year that Madonna released her hit "Take a Bow" from her 1994 album, "Bedtime Stories". Williams seems to be a constant fixture in the singer's life, as he was even spotted by Page Six touring Italy with her and her kids during the summer of 2021. 

Regardless of what people might have to say about the age gap between Madonna and her boyfriends or her penchant for public displays of affection with them, she's not about to change the way she operates or conform to society's rules. "I have lovers who are three decades younger than me. This makes people very uncomfortable. I feel like everything I do makes people feel really uncomfortable," she shared in a 2017 interview with Harper's Bazaar. "I believe women should own their sexuality and sexual expression. I don't believe there's a certain age where you can't say and feel and be who you want to be," she added elsewhere in the interview.

This may be what we would expect from Madonna, but we do have one other question: would she ever try marriage a third try? 

Madonna knows better than to make the same mistake twice

Madonna has rarely spoken up about her marriage and divorce from Guy Ritchie, but in 2012, she did tell Newsweek that their time together wasn't the fairytale she expected it to be. Sharing a little insight into their relationship, Madonna said that her marriage to Ritchie made her question the idea of "perfect love." She put it this way, "Because when you start off, everything's great and lovely, and the person you've married is flawless, and you're flawless. Then time goes by, and you share a life, you have children, and there are cracks in the veneer. It's not as romantic as it used to be. You think, 'This isn't what I thought it was going to be,' and 'How much am I willing to sacrifice?"

That's a sentiment that Madonna's other ex, Sean Penn, might agree with. Around the same time that Penn announced his divorce from actor Leila George, per People, Madonna shared an Instagram photo of her wearing a post-it on her forehead with Penn's name on it. Her love life might not be perfect, but as her ex Ritchie said, she can certainly outperform the entire field of them.