Madonna, 66, Proves Age Means Nothing When It Comes to Love

In a world that loves to judge women for how they age — and especially who they date — Madonna continues to break every rule. In her latest chapter, the pop legend once again proves that confidence has no age limit.

Madonna thinks her two marriages were a big mistake.

The singer has been married twice in her life. With her first husband, Sean Penn, they lived together for four years and separated in 1989. After the divorce, Penn and Madonna managed to keep their friendship and still support each other to this day. The former husband and wife even admitted on several occasions that their love for each other has not disappeared over the years.

Madonna’s second marriage, to director Guy Ritchie, lasted eight years. The singer later said that this was the last time she dared to walk down the aisle, and she would never take this step again.

Madonna noted that while married, she sometimes felt like a prisoner. She couldn’t just be herself, always having to put on a persona. Now the singer believes that no amount of love can save a relationship if the partners don’t accept each other and are uncomfortable together. The only thing she has no regrets about is her children. She is truly proud of all six of her offspring and considers them the biggest achievement in her life.

And even though Madonna doesn’t plan to ever get married again, she sometimes misses some of the aspects of family life. Married people don’t have to make decisions alone and can always feel part of a small, closed circle of people.

The singer never set out to choose partners younger than herself.

Since her breakup with Guy Ritchie, Madonna has favored younger partners. From 2019 to 2022, she was in a relationship with professional dancer Ahlamalik Williams, who was 36 years younger than her. Their romance caused a lot of controversy, although Williams’ father didn’t understand why people were making such a fuss about his son’s love life. After all, love has no age limits.

The singer herself jokingly notes that she has managed to build a very unusual family. “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,” says Madonna.

Madonna admits that she never set out to choose her partners based on their age. “I didn’t choose to, you know, I didn’t, like, write down on a piece of paper — I’m now going to have a relationship with a younger man. That’s just what happened. I just met someone that I cared for, and this happened to be his age,” the singer said. One of the star’s friends noted that Madonna feels young and full of energy, and therefore meets such partners. She just gets bored with people her own age.

Madonna’s current boyfriend: Akeem Morris.

Madonna (66) and Akeem Morris (29) have been dating since mid-2024. Their relationship progressed through public outings, social media tributes, and family events. Engagement rumors emerged after Madonna was seen with a large diamond ring in Tokyo this January. As of today, they are still together and showing strong signs of commitment, though no official engagement has been announced.

• Identity and background
  Akeem Morris is a 29-year-old Jamaican former footballer (soccer player), born May 2, 1996, in Spanish Town, Jamaica. He moved to New York in 2014 to study political science at Stony Brook University, where he also played on the college soccer team. He later played for Oyster Bay United FC in New York.

How they met
The couple reportedly first connected in August 2022 during a photoshoot for Paper magazine. Their relationship became public in July 2024, with the two appearing together during Madonna’s Fourth of July celebrations.

• Recent public appearance

Madonna rang in her 66th birthday in true queen-of-pop style — with a romantic getaway to Italy alongside her boyfriend, Akeem Morris.

On August 16, the iconic star was spotted strolling through the picturesque streets of Portofino. Morris walked proudly beside her. A private celebration was planned at the luxurious Dolce & Gabbana estate. Before the party, the couple joined friends for a relaxed, sunlit lunch.

Madonna isn’t alone in rewriting the rules of love. Lady Gaga finding forever outside Hollywood and Halle Berry becoming a mom at 41 and 47, then finding love after three divorces. These women prove — it’s never too late to love on your own terms.