Sean Penn’s Daughter, Dylan, Sounds Off On Madonna Rumors

Sean Penn’s daughter, Dylan Penn, is setting the record straight about her father and his ex-wife’s, Madonna’s, relationship. Rumors started swirling about the pair again after Penn was spotted at Madonna’s New York concert during her Rebel Heart tour. At the time, he showed up with his daughter, Dylan, and the three gathered backstage, with Penn introducing Dylan to the MDNA singer.

Now, Dylan, 24, is telling Entertainment Tonight that her father (Sean) and Madonna are “just friends.” Dylan only had the best things to say about Madonna.

“She’s incredible. She’s 50-something years old, and she’s doing it like she’s 20.”

Of their relationship, Dylan said, “I think he just really admires her work. They’re just really good friends and [I think] it’s sweet that they can have this relationship.”

Back in 1989, the two were estranged when Madonna filed for divorce. The pair wed in 1986, but they only lasted for three years due to their tumultuous relationship, which was constantly in the tabloids because of the volatile nature. Back then, Penn was charged with assault for getting into a physical altercation with Madonna, but now they’ve found a new normal — 30 years later.

During Madonna’s stop in New York, she dedicated the song “True Blue” to her ex-husband, Sean. The lyrics are incredibly telling.

“Keep you apart, deep in my heart. Separate from the rest, where I like you the best. And keep the things you forgot.”

During a concert, Madonna confessed that Penn wrote her a letter explaining that after 30 years, he finally “got” her as an artist. Back then, he was jealous of her dancing on stage with her male dancers, but now understands her work as an artist. Madonna told the crowd, “He finally appreciates my art. And that is what I have to say about marriage, okay? Thirty years later.”

Penn was sighted at another Madonna concert in Vancouver recently. This time, he was seated next to comedian Amy Schumer. A source told Radar Online that the actor “gazed adoringly at his ex from the audience.” The outlet said that Penn reserved a room in the same Vancouver hotel that Madonna was staying at, and a rendezvous happened. Additionally, the pair met up during a New York screening.

Back in August, Madonna reminisced about Sean on her public Instagram account. In honor of their birthdays, Madonna’s August 16, and Penn’s August 17, the pop diva posted an old TBT of the two, shot by the late photographer Herb Ritts.

Madonna and Sean Penn
Although Sean Penn’s daughter, Dylan, who he shares with his ex, Robin Wright, didn’t divulge any further details about his relationship with Madonna, she did tell ET about getting a chance to meet Madonna during her stop in New York. For Dylan, it was the first time she met the pop icon. She said of the experience, “It was kind of surreal to meet her. Like, my dad’s ex-lover.”

Back in January of 2015, while he was still engaged to Charlize Theron, Sean Penn told Esquire U.K. that it would be his “first marriage.”

“You say I’ve been married twice before, but I’ve been married under circumstances where I was less informed than I am today. So I wouldn’t even consider it a third marriage, I’d consider it a first marriage on its own terms if I got married again.”

As for whether or not Penn and Madonna will reunite, word is still out, but Madonna’s friends want it to happen. As the Inquisitr reported, “Madonna’s friends wish she’d get back with Sean. He will always be the love of her life.”

[Photo by David Buchan / Getty Images]