Madonna and Sean Penn called it quits in 1989, but it appears that the popular ex-sweethearts are planning to rekindle their romance after they were seen together again. Several reports claim that Sean was present during Madonna's Rebel Heart Tour in Vancouver and NYC.

Sean was pictured watching Madonna during her show beside actress Amy Schumer on Wednesday, Oct.14. It was a rare sighting as he was caught gazing at his ex admiringly, Radar Online reports. The two made headlines when the "Like A Virgin" hitmaker told her fans that Sean wrote him a letter telling her that he nows appreciates her art.

Madonna and Sean were spotted together for the first time in Septemeber, three months after the latter split with Charlize Theron. Since then the duo triggered speculations that they could be rekindling their old romance. Things have stepped up a gear when a source told the aforementioned site that Madonna and Sean booked the same hotel during the singer's Vancouver tour.

Insiders told the site that "their tour of love will continue this fall, as Penn was booked into the same hotel as the pop queen for her stays in Vancouver on October 16." The insider went to add that Sean could follow Madonna to Los Angeles for the last leg of her concert. There's also a possibility that Madonna and Sean could fly together to Europe for her performance on Oct. 29.

In September, Madonna and Sean reportedly hung out during the singer's Madison Square concert. During the time, the 55-year-old "Mystic River" star even introduced her to his daughter, Dylan Penn, Us Weekly reports.

During her Madison concert, Madonna spoke about her former husband on stage and even dedicated the song "Secret" to the special guest, TMZ reports.

"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!" she said of Penn. "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, okay!? Thirty f--king years later."