Jenna Bush Hager's Funniest 'Today' Moments, Confessions

Today fans can always count on Jenna Bush Hager to make them laugh during each episode of the series. The former first daughter often shares hilarious stories about her famous family and makes shocking confessions on the program. Her candidness is part of the reason why viewers can’t get enough of the daytime talk show.

Jenna began working as a correspondent on Today in 2009. When Kathie Lee Gifford left the show a decade later, the former teacher’s aide took her place at the news desk as an official cohost. Next to news veteran Hoda Kotb, Jenna quickly settled into the role and proved to be such a natural in front of the camera.

The Texas native grew up in the spotlight as the daughter of former President George W. Bush and former first lady Laura Bush. Along with her twin sister, Barbara, she navigated being a member of America’s first family in her early 20s. Years later, Jenna revealed some secrets about their time in the White House on Today, including what it was like dating during that time. She described the early stages of her romance with her now-husband, Henry Hager, and how she would sneak him in and out of the White House.

“My parents were traveling, and I was staying there,” Jenna recalled during a conversation with Hoda in November 2022 on the show. “We’d gone out to the bars and, like all relationships do, it reached a certain level. Henry said he woke up and he looked around and he was, like, ‘Aaaaaaaah’ because he worked for my dad.”

It wasn’t the first time Jenna revealed details about dating while living in the White House. During a February 2021 episode of Today, she shared a story about her and Henry’s most disastrous date.

“My worst first date involved the Secret Service, let’s just leave it at that,” she said. “It was with Henry and his car ran out of gas and went backward and hit the Secret Service.”

The New York Times bestselling author and the businessman got married in 2008 and welcomed three children together: Mila, Poppy and Hal. Just like their famous mom, the kiddos all have a great sense of humor. In December 2022, Mila appeared on an episode of Today to reveal some of her mom’s biggest secrets.

“One time she was laughing in our living room, and she peed her pants!” Jenna’s eldest daughter told viewers during the episode. “You changed your pajamas!”

Keep scrolling for a roundup of Jenna’s funniest moments on Today over the years.

Jenna’s Shocking Underwear Confession

During a November 2022 broadcast, Jenna shared that she “never wears underwear.” Hoda brought the topic up after sharing a dressing room with her costar backstage.

“I think it makes a more pretty silhouette!” the mom of three confessed. “I also think you don’t have to pack as much. There’s a lot of pros to it!”

Jenna kept a smile on her face throughout the segment, proving she is a good sport. She even predicted how her parents were going to react to her candid confession.

“You promised me you wouldn’t do this! There’s a lot of people here!” the TV personality joked to Hoda. “I’m sure my mom has never been more proud.”

The Truth Behind the Viral Bush Family Photo

By now, most loyal Today viewers have seen the iconic throwback photo of the Bush family dressed in red, white and blue outfits. In honor of July 4, 2022, producers decided to resurface the picture and share it on the program. “Look at your outfit,” Hoda said through laughter, to which Jenna responded, “I know, please stop.”

The pair couldn’t contain their giggles over Jenna’s headband, bangs and American flag T-shirt. Finally, the journalist shared the inspiration behind her look back then. “I was just desperate to be Kelly Taylor on 90210,” she revealed.

Steamy Text Messages Gone Wrong

Justin Slyvester joined Jenna at the news desk for a special segment of “He Said, She Said” in July 2022. The game required the costars to share their honest opinions about an array of topics, including “U up?” text messages. While most would consider the text messages to be sexually suggestive, Jenna’s rant was all too real for parents watching at home.

“I’ll just tell you something about a ‘U up?’ text,” she began. “When you are married to somebody for an extended amount of time, you’re no longer texting in the middle of the night.”

The beloved journalist added, “You hear a child calling in the middle of the night from some distant place. You roll over and you elbow the person, and you say, ‘You up? You up, let’s go!’ It’s very sexy.”

Jenna’s Celebrity Crush

In June 2022, Justin filled in for Hoda again and got right down to business asking Jenna some hard-hitting questions about pop culture. When asked to choose who was hotter between Austin Butler and Harry Styles, the NBC star revealed that she had a crush on Austin. After attending a screening of Elvis with Henry, he explained he was “not comfortable” with Jenna interviewing Austin, who starred in the titular role.

To comfort her partner, Jenna said, “Honey, you have not been jealous of me in years.” Henry replied, “That’s the best-looking man I’ve ever seen in my life.” The longtime couple laughed it off, with Jenna agreeing that Austin is “so handsome and so kind.”

A Hilarious Movie Theater Blunder

While sitting down with Today costar Willie Geist in February 2022, Jenna recounted a funny experience at a movie theater. Back in 2009, she took her grandfather George H.W. Bush to see Brüno, starring Sacha Baron Cohen. She didn’t realize the comedy film had nude scenes, leading the Secret Service agents that accompanied them to the theater to cover their eyes for most of the film.

“The worst part is, like, right away he was like, ‘Do we leave? Do we have to leave?'” she recalled about her late grandfather before revealing that they stayed for the entire film and enjoyed it.