List of All the Men Madonna dated in Her Life! Why She Regrets marrying twice?

Updated On March 18, 2024 | Published By: Selina shamp | In Child , Divorce , Relationship

source: Pop Sugar

Madonna is sharing her terrible experience of marrying twice in her life.
In a Q&A session with answered 50 questions sent to her by fans on her YouTube channel in a candid confession.
Learn about the relationship timeline of Madonna and her terrible experiences in her married life.

Queen of Pop Madonna, 64 regrets one thing in life and that’s her marriage! In a recent Q&A session, the legendary performer revealed her upcoming album, career to date, guilty pleasures, and biggest regrets.

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Why does Madonna regret getting married twice in her life?

Like a Virgin album creator, Madonna was not happy with how her marriage went on in her life. Grammy award winner for album Confessions on a Dance Floor had been married twice but did it work out? She was obsessed with sex only.

The sexual icon of the postmodern era was first married to actor Sean Penn for 4 long years between 1985 to 1989. They divorced on abuse and assault allegations and even once Penn demanded $10 M on legal separation.

After the failed marriage she again wedded another legendary actor, Guy Ritchie in 2000 but terminated their marriage after around 7 years of marriage and got divorced in 2008.

She confessed that marriage was not the best idea and couldn’t express herself as an artist during her second marriage. She also disclosed in 2015,

“There were times I felt incarcerated. I wasn’t really allowed to be myself. You’ve got to find someone who accepts who you are and is comfortable with that.”

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Madonna’s recently single life after her beau Ahlamalik Williams moved out of her house

Her confession of regretting having tied the knot earlier comes a few months after breaking up with her age-gap boyfriend, Ahlamalik Williams, 28. They were seeing each other for 3 years even after having 36 36-year age gap.

The Like A Prayer singer met this recent beau in 2015 at her Rebel Heart Tour 2015 but their low-key romance got public attention only in 2019. They were living together but after January 2022 they had differences. So they were separated by April 2022 on mutual terms and had no harsh feelings.

Also, Read Madonna, 63 splits with boyfriend Ahlamalik Williams, 28 after 3 years of togetherness

List of all the men that Madonna dated! Also, who are her baby daddies?

Digging back to the past, Madonna has been romantically linked to many celebs like Jellybean Benitez, Mark Kamins, Jean-Michel Basquiat, and Dan Gilroy.

Her past boyfriends also include model Tony Ward, rapper Tupac Shakur, basketball player Dennis Rodman, model Jesus Luz, Andy Bird, and John Albright. John Kennedy jr., Brahmin Zaibat, and Idris Elba are her other boyfriends back in the past.

Madonna kids — Madonna’s rare picture with her six children (source: Eonline)

She also dated her boyfriend Carlos Leon late 1994 until mid-1997, who is also her daughter’s daddy. Among six children of Madonna, biological daughter, Lourdes Leon, 25 born in October 1996 is the eldest.

Her son Rocco Ritchie, 22 is born in her marriage with Guy Ritchie. Her other four adopted kids, are David in 2006 and Mercy in 2009. She also adopted twins Estere Ciccone and Stelle Ciccone in 2017.

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