Jelly Roll Shares Emotional Talk He Had with Daughter, Who’s Now the Same Age He Was When He Was Arrested (Exclusive)

Jelly Roll was just 14 years old the first time he was arrested — but he’s not worried that his teenage daughter Bailee will make his same mistakes.

In this week’s cover story, the Grammy-nominated singer, 39, opens up to PEOPLE about the conversations he has with daughter Bailee, 16, recalling one recent chat where he reminded her just how much potential he sees in her.

“[I said], ‘I don’t judge you based on what you do. I judge you based on what I know you’re capable of,’ ” he recalls. “‘You’re so much smarter than I was at 16. You’re so much better, so much more emotionally intelligent. You can read a room so much better. So don’t try to talk your way out of getting in trouble, Miss Sassy, by weaponizing my past.’”

Jelly, who is also dad to 8-year-old son Noah, says Bailee is “totally ahead” of where he was as a teenager, and that he feels confident she has a bright future ahead.

“When I look at what she does that I consider horrible, I look back at what I was doing at 16, and I’m like, ‘Oh man…’ When I’m hard on her about stuff or a little pushy, she knows it’s from love,” he says.

The “Winning Streak” singer and his wife Bunnie Xo have had full custody of Bailee since 2017 due to Bailee’s mom’s struggle with drug addiction (Jelly has since said that Bailee and her mom are working on mending their relationship).

He and his daughter remain close, and she was by his side earlier this month when he performed at the 2024 CMA Awards. Jelly was behind bars when Bailee was born, and has said that her birth was a turning point in his life.

“We were really, really close before it exploded, but she understands what it’s doing for her future and the family’s future,” he says. “She’s a really hammered down kid. She’s been in the same public school district for 10 years and had the same friends since me and Bunnie have had custody of her. I think a lot of that has helped.”

Bailee recently appeared on Bunnie’s Dumb Blonde podcast, and revealed that she hopes to go to Columbia University after high school, with a plan to become a criminal defense lawyer.

“That’s where I wanna go, and I wanna study law. As for music, I don’t have any plans for it right now,” she said.

The teen also revealed that most of her classmates have moved past the fact that she has a famous dad.

“We’re all kinda used to it,” she said. “He’s come to football games, and whatever. So I think everybody’s kind of over that ‘Oh, my God.’ And, also, people are kinda just know not to f— with me. I’m just not the one. So it’s pretty easy. Other than that, making new friendships is hard, but I just don’t do that anymore.”

For more on Jelly Roll, pick up the latest issue of PEOPLE, on newsstands everywhere now.