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- Learn more:✕This summary was generated using AI based on multiple online sources. To view the original source information, use the "Learn more" links.Madonna has been in the spotlight for decades and has had a handful of high-profile relationships over the years. The Queen of Pop has been married twice — first to Sean Penn from 1985 to 1989, then to Guy Ritchie from 2000 to 2008.people.com/music/madonna-dating-history/If fans recall, Madonna's been married two times, first to Oscar-winning actor Sean Penn, to whom she was married from 1985 to 1989, and then to director Guy Ritchie, in 2000. The pair, who share sons Rocco, 22, and David, 16, split in 2008 after nearly eight years of marriage.www.etonline.com/madonna-talks-past-marriages-t…Madonna has been married two times. First to Academy Award-winning actor and director Sean Penn from 1985 to 1989. She then got married to Guy Ritchie in 2000 but the two ended up splitting in 2008.www.sportskeeda.com/pop-culture/how-many-time…
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