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.
PHOTOS: Sean Penn and Madonna together
Sean Penn Madonna
Exes Madonna & Sean Penn spark dating rumors after actor is spotted at another concert
NEW YORK, NY - SEPTEMBER 24: (Exclusive Coverage) Sean Penn and Madonna attend Madonna and Steven Klein secretprojectrevolution at the Gagosian Gallery on September 24, 2013 in New York City. (Photo by Kevin Mazur/Getty Images)
NEW YORK CITY - JULY 13: Actor Sean Penn and singer Madonna on July 13, 1987 leave for an after party for Madonna's Who's That Girl World Tour Concert at Madison Square Garden in New York City. (Photo by Ron Galella, Ltd./WireImage)
Madonna & Sean Penn in Los Angeles, California (Photo by Barry King/WireImage)
NEW YORK CITY - AUGUST 28: Singer Madonna and actor Sean Penn leave for the Lincoln Center's Workshop Production of 'Goose and Tomtom' Opening Night Party on August 28, 1986 at Mitzi E. Newhouse, Lincoln Center in New York City. (Photo by Ron Galella/WireImage)
Madonna and Sean Penn (Photo by Ron Galella/WireImage)
NEW YORK - AUGUST 1986: Acting couple Madonna and Sean Penn leave rehearsals for their play 'Goose and Tom Tom' in August 1986 in New York City, New York. (Photo by Vinnie Zuffante/Michael Ochs Archives/Getty Images)
Sean Penn and Madonna at the Lincoln Center in New York City, New York (Photo by Ron Galella/WireImage)
Sean Penn and Madonna (Photo by Ron Galella/WireImage)
Singer Madonna and actor Sean Penn on the set of the film 'Shanghai Surprise', Hong Kong, February 12th 1986. (Photo by Dave Hogan/Getty Images) *** Local Caption ***
Sean Penn and Madonna at the Elaine's Restaurant in New York City, New York (Photo by Ron Galella/WireImage)
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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.