Jenna Bush Hager’s Unexpected Confession: The One Regret She’s Carried Since High School. .QN

Jenna Bush Hager may be one of television’s most confident and outspoken personalities today, but the Today with Hoda & Jenna host is looking back on a time when courage didn’t come quite so easily. During a heartfelt segment of the show, the 42-year-old revealed a personal truth from her teenage years that surprised even her co-host, Hoda Kotb.

Growing up as the daughter of former President George W. Bush, Jenna’s life was far from ordinary. Yet when it came to high school, she was just like any other teenager—eager to belong, but quietly battling self-doubt. She shared that her “one big regret” was never joining the school’s drama program. “I was too nervous,” she admitted. “Too scared to get on stage.” Despite her outgoing personality, Jenna revealed she often held herself back, choosing comfort over risk.

Instead, she channeled her energy into everything else—running track (“poorly,” she laughed), writing for the school newspaper, playing field hockey, and joining student council. “I loved being part of a team,” she recalled. “I really, really loved it.” But despite the accomplishments, that lingering “what if” never faded. “I always tell my kids,” she said, “don’t be afraid to try something that scares you.”

Jenna’s reflections struck a chord with viewers who’ve watched her evolve from the shy first daughter of the early 2000s into a bestselling author, TV personality, and advocate for embracing life’s messiness. Her honesty on air offered a rare glimpse into the vulnerability that shaped her resilience — a reminder that even those who seem effortlessly confident have had moments of hesitation.

When Hoda Kotb expressed surprise, saying she assumed Jenna was “always outgoing,” Jenna nodded in agreement but emphasized that being outgoing didn’t mean she wasn’t afraid. “You can be loud, and still be nervous,” she said — a sentiment that resonated deeply with audiences and parents alike.

Now a mother of three — daughters Mila, 10, Poppy, 8, and son Hal, 4 — Jenna said she hopes her children will learn from her hesitation. Rather than encouraging her daughters to focus on marriage or motherhood, she motivates them to chase passion and purpose. Mila, she revealed proudly, dreams of becoming both a writer and a lawyer, while Poppy is already showing a flair for acting — a dream Jenna once had but never pursued.

Her story is more than nostalgia; it’s a lesson in second chances. In sharing her biggest regret, Jenna Bush Hager quietly reminded the world that the courage to begin doesn’t come from confidence — it comes from curiosity. And sometimes, the dreams we put aside in our youth have a way of returning through the next generation.