Madonna Talks Past Marriages to Guy Ritchie and Sean Penn: 'Weren't the Best Ideas'

Guy Ritchie and Madonna; Sean Penn and Madonna
Dave Hogan/Getty Images; Ron Galella/Ron Galella Collection via Getty Images

The 64-year-old singer spoke about her marriages in a YouTube video, where she answered fan questions about her music, life and more.

Madonna is getting real about her past relationships. In a video shared to the music legend's YouTube channel, Madonna answered 50 questions from fans about her new album, Finally Enough Love, as well as about her life and career.

When asked about a decision she now feels wasn't the best idea, Madonna kept it short and sweet.

"Getting married," she said. "Both times."

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.

Madonna's spoken about both of her marriages. In 2011, shortly after her split with Ritchie, she told Details magazine that she didn't regret their marriage, instead calling it a "soap opera" she lived in for "quite a long period" of her life.

"It's definitely not something I regret," the 64-year-old singer said at the time, though she's now singing a slightly different tune in her YouTube video. "The experience was ultimately very positive. I love the kids that came out of it, but you move on, don't you? You're right, I stepped into a soap opera, and I lived in it for quite a long period of my life."

Where her current relationship with Ritchie stands, is unclear.

As for Penn, Madonna has openly praised the Mystic River actor. In 2016, Madonna attended Penn's annual Help Haiti Home gala where she showered him with love.

"I want to say [to] Sean that I loved you from the moment that I laid eyes on you," she said on stage at the event. "And I still love you just the same."

She even jokingly offered to re-marry him.

The feeling appears to be mutual for Penn, who in 2018 told Stephen Colbert while appearing on The Late Show, that he still has lots of love for the pop star. In a segment called, "Sean Penn-y For Your Thoughts," he was asked by Colbert to pick between Madonna and pop princess Britney Spears.

"Ah, I love my first wife very much," Penn said of the 59-year-old singer. "There’s no [comparison]…you don’t compare those things."

While she has some regrets where her love life is concerned, one thing Madonna told fans she had no qualms about, is her children. In addition to Rocco and David, Madonna is mom to Lourdes, 25, Mercy, 16, and nine-year-old twins Stella and Estere.

She called her "six amazing children," the achievement in her life she is the proudest of.

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