Madonna Reportedly ‘Shocked’ By Ex Sean Penn’s Natural Aging

The singer, who once called the actor the love of her life, is said to be unaccustomed to that reality, particularly given her own efforts to maintain a youthful appearance over the years.

Madonna and Penn were married from 1985 to 1989 after meeting while filming her music video “Material Girl.” Despite their volatile union, the two have remained loosely in touch over the years.

With over four decades having passed since Madonna split from ex, Sean Penn, the two have both grown older and are now in their sixties.

While Penn’s recent public appearances have shown him embracing natural aging by letting his hair go fully gray and appearing carefree about his increasing wrinkles, Madonna has chosen the path of rewriting the rules of beauty and defying time itself with what appear to be multiple cosmetic interventions.

However, for Madonna, seeing Penn let himself age naturally has come as a shock to her, one she is currently still grappling with

“This is not Sean as she remembers him,” a source said of the singer recently seeing her ex, according to a report. “She couldn’t believe it — natural aging, gray hair… It’s just not her Sean.”

“She’s used to controlling every look, every image,” the insider added. “Seeing Sean age naturally — without filters, fillers, or Hollywood tricks — was a shock to her system. She’s not used to that reality.”

Penn’s natural aging is not the only thing Madonna appears to be shocked by, as recent reports have revealed that she does not agree with his lifestyle.

The 65-year-old actor was seen repeatedly smoking throughout the 2026 Golden Globe Awards in Beverly Hills on Sunday, January 11.

Despite being approached on three occasions by event staff and asked to put out his cigarette, he allegedly refused to comply and continued the behavior.

Seeing Penn act in this manner and remain firmly entrenched in his smoking habits has deeply worried Madonna.

“It’s brutal to watch what Sean is doing to himself right now. He seems to be in self-destruct mode,” a source recently told Globe. “He acts like he’s bulletproof, but it’s obvious this lifestyle is taking a huge toll on him.”

Madonna’s marriage to Penn lasted just four years after meeting on the set of “Material Girl” in 1985.

Despite the entire marriage being quite tumultuous, the singer was reportedly “genuinely in love” with the actor while it lasted, according to Sharon Oreck, who produced the music video.

“She was genuinely in love with him, but it felt as if the attraction between the two of them was fueled by the public. He was the budding movie star, she was the budding rock star, and the public demanded that they come together,” the director said in an  archival audio featured in the pop goddess documentary “Becoming Madonna.”

“It was like a bomb went off,” Oreck said of the duo’s romance. “America’s bad boy and America’s bad girl.”

Madonna appeared to hint that she still has affection for Penn when she was seen referring to him as the love of her life in her documentary.

However, it appears the actor feels differently, as he bluntly responded to the statement during an appearance on Louis Theroux’s podcast in mid-2025, according to the Daily Mail.

“I remember what she said,” Penn said of the remark when asked by his host if he recalled it from the documentary.

He added, “She’s very sweet. Look, she’s been a good friend for a lot of years.”

He went on to suggest that their marriage was a mistake despite the whirlwind relationship they had.

“It didn’t take us long to realize that we had mistaken a good first date for a wedding partner,” the actor said.

Penn added, “It didn’t take us long to recover after we got divorced, maybe a year, in a friendship. I have a lot of fond memories of it – it’s not all jail.”

“But there was a lot of alcohol, and she’d be fairly accusing me of that,” he further noted about his relationship with Madonna.