The duo -- who first connected in 1985, tied the knot after just six months and pulled the plug on their rocky romance in 1989 -- are reportedly hooking up on various stops of Madonna's Rebel Hearts tour.
The "Milk" star was photographed in the audience alongside Amy Schumer at his ex-wife's Vancouver show on Oct. 14. He was also spotted at one of her performances in New York City on Sept. 17. (He reportedly introduced his daughter, Dylan Penn, to the pop star backstage following the show.)
Now the volatile actor intends to join Madge on the road, Radar reports. He's reportedly booked into the same hotel as the "Like a Virgin" singer in Vancouver and plans to follow her to Los Angeles. Sean could even join her on the European leg of her tour later this month, a supposed insider tells the website.
On Sept. 29, Madonna opened up about her ex-husband while performing at the Barclays Center in New York City.
"I did a show at Madison Square Garden the other night if you heard about it. And my ex-husband was there! Could you imagine?" she told the crowd. "He had been at my show 30 years earlier when I was at Madison Square Garden, and he was very upset with me for wearing a costume that was too revealing. That's not a lie. Anyway, after the show he wrote me a letter and said he finally appreciates my art. And that is what I have to say about marriage, OK? Thirty f------- years later."