Penn, 55, was seen gazing adoringly at his ex-wife from the front row of her concert in Vancouver, Canada, Wednesday night, right next to Madonna's new pal Amy Schumer. At one point, he looked on as Madonna, 57, toasted Schumer with a shot in the middle of the show.
Schumer opened for the pop icon during the New York City leg of her Rebel Heart tour last month, where Penn was previously spotted taking in one of his ex-wife's performances. As the GRAMMY winner took the stage for her second night at Madison Square Garden, Penn sported a sweet smile when the Material Girl broke into her 1986 hit, "True Blue," which was inspired by him.
Madonna's four-year marriage to Penn came to a tumultuous end in 1989 after accusations that he abused her. Madonna then gave wedded bliss a second chance in 2000, when she wed director Guy Ritchie. That marriage ended in 2008.
Meanwhile, Penn wed actress Robin Wright in 1996 before splitting up in 2010. He was reportedly dumped by his former fiancée, Charlize Theron, 40, in May.