Sean, who divorced the 57-year-old singer in 1989 after four years of marriage, took Dylan, 24, to cheer her on from the front row during her concert at New York City's Madison Square Garden before taking the model backstage to meet the star, reported E! Online.
"He introduced Dylan to Madonna. It was the first time they had met."
The "Mystic River" star, who divorced Dylan's mother Robin Wright in 2010 after 14 years of marriage, was also captured on camera by several fans smiling widely while Madonna performed her classic track "True Blue" during the gig, which she dedicated to him when it was released in 1986.
The 54-year-old actor, who has been single since splitting from former fiancee Charlize Theron in June, previously revealed he and his first wife are still "very friendly.
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