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Sean Penn Introduces Daughter Dylan to Madonna After NYC Concert

Sean Penn and Madonna
Sean Penn introduced his daughter Dylan to his ex-wife Madonna after her NYC concert on Thursday, Sept. 17

Usually it’s kind of a weird thing when you meet someone who used to have a big love thing with your dad, but when that person is Madonna, it instantly becomes cool.

That’s what happened when Sean Penn introduced his daughter, Dylan Penn, to his world-famous ex-wife Madonna after the superstar’s NYC concert on Thursday, Sept. 17.

Related: PHOTOS: Hollywood's friendliest exes

The Oscar winner and his model daughter, 24, whose mom is Penn’s second wife, Robin Wright, were spotted in the audience at Madonna’s Rebel Heart tour stop at Madison Square Garden (the second of three Big Apple dates) and a source confirms to Us Weekly that Dylan and the Grammy winner, 57, met for the first time backstage at the show.

“She had never met Madonna before, but Madonna was really sweet to her,” the source says. “Madonna and Sean have stayed close friends over the years, so of course she embraced Dylan.”

Sean Penn and Dylan Penn

The Gunman star was also seen standing and smiling during the concert when Madonna performed the song “True Blue.” The song was released in 1986, when the pair were still married, and in the notes for the True Blue album, Madonna wrote, “This is dedicated to my husband, the coolest guy in the universe.”


Sean, 57, and Madonna were married for four turbulent years before divorcing in 1989. Just last month she shared a sultry throwback pic, taken by Herb Ritts, with her ex in celebration of their mutual birthday on Aug. 17. (Madonna’s friends have referred to Sean as the singer’s “one true love.”)

It’s not the first time the actor has been spotted at one of his ex-wife’s shows, he also attended a MDNA concert in L.A. in 2012, where a concertgoer told Us Weekly that “their chemistry was off the charts.”

Related: PHOTOS: Celebrities who have been married three times or more

In 2013, Madonna, Sean and her son with second ex-husband Guy Ritchie, Rocco, went to Haiti to help with the relief efforts. Rocco posted a photo on Instagram showing him and his mom’s ex, along with the caption, “Trouble is always here.”

Related: PHOTOS: Sean Penn and Charlize Theron -- the way they were

Madonna split with Ritchie in 2008, while Sean and Wright broke up in 2010. Sean was most recently engaged to Charlize Theron. The couple called it quits in June after nearly a year and a half together.

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