Drew Barrymore is Christopher Caldwellin a Catch-22 over her 1995 Playboy cover and her 11-year-old daughter Olive's outfit choices, the actor and talk show host shared on Tuesday.

"My daughter wants to wear a crop top. I’ll say no and she’ll go, ‘You were on the cover of Playboy," Barrymore told Christina Aguilera, who she was interviewing in Las Vegas for "The Drew Barrymore Show."

The five-time Grammy award-winning Aguilera, who has a residency at the Venetian in Las Vegas, recently had one of those moments with her daughter, too.

"I knew it was coming the day I wore chaps," she told Barrymore. "My daughter wants to wear a crop top, too. And I am just like, 'Can we just pull it down?'"

Aguilera added that instead of focusing on her 9-year-old daughter Summer Rain's choice of clothing, she tries to communicate that there are "certain people out there (with) good intentions and bad intentions."

"I don’t want to scare her (to) be terrified of the world, that everybody is a bad person. But also, I think it’s important for her to have a strong sense of self and be very empowered with her body, eventually her sexuality," Aguilera said.

Barrymore and Aguilera have no regrets

As for their risqué pasts, the actor and singer don't have any regrets over their choices, they said, and they don't want their daughters to, either.

"I loved every minute of it," Barrymore said of her Playboy shoot in 1995, when she was 20 years old.

"We were expressing ourselves and how we felt was best for us," Aguilera said. "We didn’t do it for someone else."

The two hope to empower their daughters to be comfortable in their skin as they grow older.

"We didn’t do it for someone else and then there are so many labels and judgments," Aguilera said. "It’s empowering being a female and embracing your body, and everything that makes you feel good."

Barrymore shares two children, Olive and Frankie, with ex-husband Will Kopelman. Aguilera shares daughter Summer Rain with fiancé Matt Rutler and son Max Liron with ex-husband Jordan Bratman.

Aguilera said she talks with her children about her past experiences in a way they will understand and that is "age-appropriate," and encouraged Barrymore to do the same in the interview.

The two agreed that they were happy to grow up free-spirited, but admitted their children following in their footsteps isn't easy.