Hey there, pop culture fans! If you’re a fan of the iconic ‘80s teen movies, chances are you remember Jon Cryer as the lovable and awkward Ducky from John Hughes’ masterpiece, Pretty in Pink. But did you know that this legendary actor has been busy raising a family while continuing to charm audiences on screen? From his breakout role in Two and a Half Men to his latest projects, Jon Cryer has been juggling fame and fatherhood with grace. With Andrew McCarthy’s upcoming documentary, Brats, set to premiere on June 13, 2024, focusing on the lives of ‘80s teen stars, fans are curious about what’s next for Jon—and especially about his kids.
Meet Jon Cryer’s Two Children
Let’s dive into the family life of this Hollywood legend. Jon Cryer is the proud dad of two amazing kids. His firstborn, Charlie, entered the world on June 27, 2000, during his marriage to his then-wife, Sarah Trigger. Fast forward to 2007, and Jon tied the knot with Lisa Joyner, the love of his life. Together, they expanded their family by adopting a daughter, Daisy, in 2009. It’s clear that Jon’s journey as a father has been filled with love, growth, and plenty of unforgettable moments.
Jon Cryer’s Take on Parenting: Letting Go with Grace
Earlier this year, Jon opened up about his parenting journey in a candid conversation with People magazine. He revealed a powerful lesson he’s learned over the years: sometimes, the best thing a parent can do is let go. In a world where control can feel like a necessity, Jon shared his wisdom with refreshing honesty.
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“What I’ve realized through the years is that control is just an illusion,” Jon explained in an article published on January 1, 2024. “When you bring children into this world, you’re giving them the freedom to grow into their own people. Where they go and who they become is ultimately up to them. It’s cliché, but it’s all about letting go—and recognizing the limits of what you can do as a parent. Watching your kids navigate life on their own terms is truly a beautiful thing.”
Of course, letting go isn’t always easy. Many parents struggle with the idea of their kids leaving the nest, but Jon sees it as an opportunity for growth—for both parent and child. “It’s not always easy, but there’s a silver lining,” he added. “You get to witness your children evolve into adults, and that’s a gift in itself.”

For Jon, the joy of parenting continues to evolve as his kids grow older. “Now that my son Charlie is 23, I’ve entered this amazing phase where I get to know him as an adult. It’s so rewarding to connect with him on a whole new level,” he said. “Of course, I’m always here to offer advice when he asks, but mostly, we can just be ourselves. There’s a beautiful simplicity in that.”
Jon Cryer’s Funny Take on His Kids’ Reaction to ‘Two and a Half Men’
While Jon’s career has been nothing short of stellar, his kids aren’t exactly fans of his work—or at least they don’t admit it. After wrapping up his time on Two and a Half Men, Jon moved on to other projects, like Extended Family. But it seems that his kids have a unique perspective on his acting career.
In a hilarious interview with The Talk in March 2024, Jon joked about how his son Charlie was left “scarred” by one particularly wild episode of Two and a Half Men. “One day, Charlie was hanging out at a friend’s house, and an episode came on that was… let’s just say, deeply weird,” Jon recalled. “In this episode, Charlie Sheen and I—who play brothers on the show—wake up in the same bed, trying to figure out what happened the night before. In a flashback, I’m shirtless, wearing a Marilyn Monroe wig, and singing ‘Happy Birthday, Mr. President.’ That’s the scene my son stumbled upon. Needless to say, he has a very colorful view of my time on that show!”


