'I regret BOTH my marriages': Madonna throws shade at Sean Penn and Guy Richie, says her current obsession is 'sex' and reveals she'd be a school teacher if she wasn't a singer
Madonna did not hold back while answering 50 fan questions about her upcoming album, four-decade career, guilty pleasures and biggest regrets.
In a new video, uploaded to her YouTube channel on Tuesday, the 64-year-old pop star had a surprisingly candid answer when asked what decision she 'looks back on' and realizes 'wasn't the best idea.'
'Get married. Both times!' the Holiday singer stated, alluding to her past marriages to Sean Penn, 62, from 1985 to 1989, and Guy Ritchie, 53, from 2000 to 2008.
![Cool girl: Madonna did not hold back while answering 50 fan questions about her upcoming album, four-decade career, guilty pleasures and biggest regrets](https://i.dailymail.co.uk/1s/2022/08/31/00/61887189-0-image-m-101_1661900672057.jpg)
Cool girl: Madonna did not hold back while answering 50 fan questions about her upcoming album, four-decade career, guilty pleasures and biggest regrets
Madonna shares son Rocco, 22, and also shares daughter Lourdes, 25, with Carlos Leon. She adopted children Mercy and David, both 16, and twins Estere and Stelle, 10.
During the interview, she went on to reveal her 'current favorite obsession' is sex and that if wasn't a musician she would be a school teacher.
When asked how she continues to find inspiration in world that is so different than when she started, the performer said if 'you're a curious person and you're paying attention to life you'll never stop being inspired.'
The seven-time Grammy winner also raved that she would love to collaborate with Kendrick Lamar before admitting the 'hardest' part of working on her upcoming biopic 'cramming' her 'entire life into a feature-length film.'
![Open book: In a new video, uploaded to her YouTube channel on Tuesday, the 64-year-old pop star had a surprisingly candid answer when asked what decision she 'looks back on' and realizes 'wasn't the best idea'](https://i.dailymail.co.uk/1s/2022/08/31/00/61887471-0-image-m-99_1661900629880.jpg)
Open book: In a new video, uploaded to her YouTube channel on Tuesday, the 64-year-old pop star had a surprisingly candid answer when asked what decision she 'looks back on' and realizes 'wasn't the best idea'
![First marriage: Madonna was married to Sean Penn, 62, from 1985 to 1989 (pictured in 2016)](https://i.dailymail.co.uk/1s/2022/08/31/07/61897171-11162769-image-a-4_1661928616303.jpg)
First marriage: Madonna was married to Sean Penn, 62, from 1985 to 1989 (pictured in 2016)
![Second marriage: Madonna was married to Guy Ritchie, 53, from 2000 to 2008 (pictured in 2001)](https://i.dailymail.co.uk/1s/2022/08/31/07/61897169-11162769-image-a-3_1661928600562.jpg)
Second marriage: Madonna was married to Guy Ritchie, 53, from 2000 to 2008 (pictured in 2001)
Later, she credited sex for keeping her going and that she would love work to work with Britney Spears again, 19 years after releasing their hit track, Me Against The Music while rocking a plunging black minidress and fishnet stockings.
Previously, the mother-of-six admitted that she was unable unable to 'express' herself as an artist while wed to Ritchie.
'There were times I felt incarcerated. I wasn't really allowed to be myself,' she told The Sun in 2015. 'You've got to find someone who accepts who you are and is comfortable with that.'
!['Get married. Both times!' the Holiday singer stated, alluding to her past marriages to Sean Penn, 62, from 1985 to 1989, and Guy Ritchie, between 2000-2008](https://i.dailymail.co.uk/1s/2022/08/31/00/61887185-0-image-m-103_1661900717934.jpg)
'Get married. Both times!' the Holiday singer stated, alluding to her past marriages to Sean Penn, 62, from 1985 to 1989, and Guy Ritchie, between 2000-2008
![Saucy: During the interview, she went on to reveal her 'current favorite obsession' is sex and that if wasn't a musician she would be a school teacher](https://i.dailymail.co.uk/1s/2022/08/31/00/61887207-0-image-m-104_1661900747463.jpg)
Saucy: During the interview, she went on to reveal her 'current favorite obsession' is sex and that if wasn't a musician she would be a school teacher
Previously, Madonna said she would rather get 'run over by a train' than walk down the aisle again in 2009.
Meanwhile, the English film director, 53, previously told Details magazine that their time together is 'definitely not something' he regrets because he loves 'the kids that came out of it.'
Back in 1991, Madonna called Penn the 'love of her life' during a documentary and the pair have maintained a friendly relationship over the years.
![Creative: When asked how she continues to find inspiration in world that is so different than when she started, the performer said if 'you're a curious person and you're paying attention to life you'll never stop being inspired'](https://i.dailymail.co.uk/1s/2022/08/31/00/61887211-0-image-m-105_1661900775039.jpg)
Creative: When asked how she continues to find inspiration in world that is so different than when she started, the performer said if 'you're a curious person and you're paying attention to life you'll never stop being inspired'
![Answering away: The seven-time Grammy winner also raved that she would love to collaborate with Kendrick Lamar before admitting the 'hardest' part of working on her upcoming biopic 'cramming' her 'entire life into a feature-length film'](https://i.dailymail.co.uk/1s/2022/08/31/00/61887311-0-image-m-106_1661900800453.jpg)
Answering away: The seven-time Grammy winner also raved that she would love to collaborate with Kendrick Lamar before admitting the 'hardest' part of working on her upcoming biopic 'cramming' her 'entire life into a feature-length film'
![The past: Meanwhile, the English film director, 53, previously told Details magazine that their time together is 'definitely not something' he regrets because he loves 'the kids that came out of it'](https://i.dailymail.co.uk/1s/2022/08/31/00/61886963-0-image-m-107_1661900824834.jpg)
The past: Meanwhile, the English film director, 53, previously told Details magazine that their time together is 'definitely not something' he regrets because he loves 'the kids that came out of it'
![Amicable: Back in 1991, Madonna called Penn the 'love of her life' during a documentary and the pair have maintained a friendly relationship over the years](https://i.dailymail.co.uk/1s/2022/08/31/00/61887301-0-image-m-108_1661900864536.jpg)
Amicable: Back in 1991, Madonna called Penn the 'love of her life' during a documentary and the pair have maintained a friendly relationship over the years
Four years ago, the two-time Oscar winner said he 'first wife very much' when asked to between her and Britney Spears.
Madonna has six kids, including Lourdes, 25, Rocco, 22, David, 16, Mercy, 16, and twins Estere and Stella, both ten.
She is currently dating model Andrew Darnell, 23, who is 41 years his junior.
![Sweet: Four years ago, the two-time Oscar winner said he 'first wife very much' when asked to between her and Britney Spears](https://i.dailymail.co.uk/1s/2022/08/31/00/61887297-0-image-m-109_1661900896612.jpg)
Sweet: Four years ago, the two-time Oscar winner said he 'first wife very much' when asked to between her and Britney Spears
![Proud mom: Madonna has six kids, including Lourdes, 25, Rocco, 22, David, 16, Mercy, 16, and twins Estere and Stella, both ten](https://i.dailymail.co.uk/1s/2022/08/31/07/61886959-11162769-Proud_mom_Madonna_has_six_kids_including_Lourdes_25_Rocco_22_Dav-a-1_1661928246161.jpg)
Proud mom: Madonna has six kids, including Lourdes, 25, Rocco, 22, David, 16, Mercy, 16, and twins Estere and Stella, both ten
![Hot date: She is currently dating model Andrew Darnell, 23, who is 41 years his junior](https://i.dailymail.co.uk/1s/2022/08/31/00/61887605-0-image-m-114_1661901074608.jpg)
Hot date: She is currently dating model Andrew Darnell, 23, who is 41 years his junior
![Proud mom: Madonna has six kids, including Lourdes, 25, Rocco, 22, David, 16, Mercy, 16, and twins Estere and Stella, both ten](https://i.dailymail.co.uk/1s/2022/08/31/07/61887613-11162769-Proud_mom_Madonna_has_six_kids_including_Lourdes_25_Rocco_22_Dav-a-2_1661928246164.jpg)
Proud mom: Madonna has six kids, including Lourdes, 25, Rocco, 22, David, 16, Mercy, 16, and twins Estere and Stella, both ten
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