‘If Rich Men Do It, Why Is It Taboo for Her?’ Inside Madonna’s Untold History of Dating Younger Men — and the Secret Romance That Set the Template

This July, Madonna commanded center stage during the World Cup final halftime show, turning heads in a plunging corset and knee-high metallic boots.

Cheering her on from the stands alongside her children—most of whom are older than him—was her 30-year-old boyfriend, Akeem Morris. The 67-year-old pop icon and the former soccer player have been dating for two years.

While the public continues to dissect their nearly 40-year age gap, dating younger men is far from news for the Material Girl. In fact, it has been her primary preference for over four decades.

Long before Akeem Morris, or Carlos Leon (the father of her firstborn daughter Lourdes), there was Bobby Martinez.

While Martinez’s name rarely surfaces in official Madonna retrospectives, family friends and insiders reveal he left a profound imprint on her life. In the early 1980s, shortly after a young, ambitious Madonna arrived in New York City, she struck up a secret, years-long affair with the streetwise teen that set the blueprint for her future love life.

‘Madonna Just Stole Bobby Away’

Bobby Martinez was a handsome teenager of Puerto Rican descent from Manhattan’s East Side. As a young teen, he stumbled into acting with a bit part in the indie film Mixed Blood.

Around 1983, the 16-year-old graffiti artist—who tagged under the alias RP3—was introduced to Madonna by legendary pop-artist Keith Haring, one of her closest confidants.

“Madonna’s taste in young guys at that time completely mirrored Keith Haring’s: young, hot, straight Puerto Rican guys,” Gil Vazquez, a close friend of Haring, told the Daily Mail. “And what happens? Madonna shows up. Keith always told the story like Madonna just stole Bobby away from him. But you couldn’t blame Bobby — it was Madonna, the hottest pop star in the world.”

At the time, Madonna was roughly 25, with her career skyrocketing thanks to hits like Borderline and Lucky Star. While sources debate Martinez’s exact age at the start of their romance, insiders agree he was around 15 or 16.

Madonna herself dropped a hint during a 2015 interview with Ellen DeGeneres, admitting: “When I first moved to New York, I dated a 16-year-old.”

Back in a 1983 interview with Record Mirror, a then-24-year-old Madonna was even more candid:

“15 or 16-year-old boys are the best. I like lean guys who aren’t afraid to show emotion and cry. I want to caress a smooth, beautiful body, not a bodybuilder.”

Behind the Scenes and the Secret Behind the ‘BOY TOY’ Belt

Archival footage from 1984 on the set of Desperately Seeking Susan shows Martinez shadowing Madonna everywhere: clad in a tight white T-shirt and jeans, smoking cigarettes, and chatting quietly with the star between takes. He wasn’t cast in the film — he was on set purely to stay by her side.

That same year, Madonna released her monster hit Like a Virgin. On the set of the iconic video, she famously wore a white lace outfit tied together with a belt buckle reading “BOY TOY.”

New York graffiti artist Cost later confirmed the origin of the phrase: “If you look at her old videos, she wore a belt that said BOY TOY. Boy Toy was that guy RP3 [Bobby Martinez]. He wrote that tag on walls, and he was her boyfriend at the time.”

A Night With a Gun: Sean Penn’s Blind Jealousy

Pop-art icon Andy Warhol frequently recorded Madonna’s secret rendez-vous with Martinez in his published diaries. By October 1985, Madonna was married to actor Sean Penn, yet Warhol noted she was still secretly meeting Bobby behind closed doors.

Penn’s jealousy reportedly reached a boiling point. According to Christopher Andersen’s 1991 unauthorized biography Madonna Unauthorized, an intoxicated Penn once went hunting for his wife’s young lover while armed with a handgun.

Martinez later described that terrifying night: “I was at the Palladium club and heard Sean was looking for me. He walked right up to the DJ booth, and I was standing directly behind him. It was dark in the club, so he didn’t see me. But when he unzipped his jacket, I saw a gun. The guy looked completely unhinged, man. I just ran for my life.”

Wild Passion and a Tragic, Secret End

Madonna and Bobby continued to meet in secret even when the singer embarked on a high-profile affair with Warren Beatty in the late 1980s. In later interviews, Martinez didn’t hide the raw nature of their connection: “We would meet in clubs or rent hotel rooms. If she wanted sex, she’d just say, ‘Let’s go smash,’ and we went.”

However, by the late ’80s, Martinez reportedly looked exhausted and struggled with substance abuse. Unlike her future partners, he never served as arm candy on red carpets — their romance remained strictly behind closed doors.

Following the death of their mutual friend Keith Haring from AIDS in 1990, Martinez vanished from the public eye. Street artist Cost later confirmed in a blog post that Bobby Martinez had passed away years ago from an overdose.

The Lifetime Template

Since Martinez, Madonna’s dating history has featured a steady stream of younger paramours strikingly similar in vibe: Carlos Leon, Jesus Luz, Brahim Zaibat, Ahlamalik Williams, Josh Popper, and now Akeem Morris.

“She wants guys who give her foot massages, cater to her, bring flowers every day, and are up for daily intimacy,” an insider revealed.

For her part, Madonna has repeatedly addressed why men her own age hold little appeal:

“Older men are too set in their ways. To enter my crazy world, you have to be truly adventurous.”

Gil Vazquez sums up the double standard:

“Madonna is simply doing what wealthy, powerful 60-year-old men have been doing for decades. But when a 60-year-old man dates a 24-year-old, it’s considered normal. When a woman does it, it’s still treated like a taboo.”