Madonna says Lourdes moving out was worse than any of her breakups.
The Queen of Pop has 18-year-old Lourdes with her ex-partner Carlos Leon and son Rocco with her former husband Guy Ritchie. She also has adopted kids David and Mercy.
While she's been through plenty of high-profile romances, the star says seeing her eldest daughter head off to university was her lowest point.
"It was the worst day of my life," she exclaimed to German magazine Gala. "Even when my long-term relationships broke down; I've never experienced pain like that."
There have been rumours in the past that Lourdes and her mother have clashed due to her cautious parenting. And Madonna admits she can be a little overzealous when it comes to looking after her brood.
"It's a sad fact that we live in a messed up and sick world," she sighed. "It seems to get worse every year. There are so many crazy people out there!
"I really annoy my kids with my worrying."
At 56 Madonna's career is still going strong and she loves to show off what she's got in sexy magazine spreads. In a shoot for Interview last year, the star even went topless.
"The ageism in our society makes me sick!" she fumed. "Should women just disappear when they turn 50? Is there a law that says we are no longer allowed to be adventurous or experiment? That we're not allowed to feel sexy and celebrate our sexuality?"
Luckily, Madonna has plenty of loyal fans who rallied around when BBC Radio 1 was accused of snubbing her song Living for Love. The British station was forced to refute claims it had left the track off its playlist due to the singer's age.
"Thank you to all of my fans for all your support!!! It means a lot!! We are all #livingforlove (sic)," she wrote on Twitter.