Jenna Bush Hager details awkward conversation with son Hal, 7, about her ex-boyfriends

Jenna Bush Hager revealed that her son, Hal, asked about her ex-boyfriends while her husband, Henry Hager, was out of town.

The journalist recalled watching an unnamed rom-com with the 7-year-old when he inquired about the men she dated before her 2008 wedding.

“He’s like, ‘Mom, do you like anybody the way that girl likes him?’” she shared on Tuesday’s episode of “Today with Jenna & Sheinelle.” “And I was like, ‘Yes, your father.’”

Jenna Bush Hager holding Hal outdoors. — Jenna Bush Hager reflected on her 7-year-old son, Hal, asking about her ex-boyfriends. (Seen here: Bush Hager with her son.) Jenna Bush Hager/Instagram

Jenna Bush Hager and Henry Hager pose with their three children, Mila, Poppy, and Hal, on a deck outdoors. — The reporter recalled watching a rom-com with her son when he became curious about her exes. (Seen here: Bush Hager with her husband, Henry Hager, and their kids.) Jenna Bush Hager/ instagram

Hal then pushed the question a bit further, asking if Bush Hager, 44, “liked other guys before Dad.”

“I had to go through the old roster,” she joked.

Bush Hager told viewers she skipped over “all the entry levels” and only mentioned the “higher-level” boyfriends.

Jenna Bush Hager speaks in a studio with a city skyline backdrop. — “He’s like, ‘Mom, do you like anybody the way that girl likes him?’” she told “Today” show viewers on Tuesday. NBC News

Jenna Bush Hager kisses her son, Hal, on the cheek. — “And I was like, ‘Yes, your father,’” Bush Hager added, referring to her husband, Henry Hager. jennabhager/Instagram

“At some point I was like, what am I doing? Why am I doing this?” she quipped.

Hal then asked his mom why she liked her exes, to which she responded, “I don’t even remember, Hal! It was 25 years ago!”

Bush Hager admitted she continued to entertain the conversation, explaining to her son the fun of dating.

Hoda Kotb and Jenna Bush Hager with her son Hal on the set of the TODAY show. — Eventually, Bush Hager (seen here with her son and Hoda Kotb) had to go through her “old roster.” Nathan Congleton/NBC via Getty Images

Hoda Kotb, Jenna Bush Hager, and her son Hal on the — “At some point I was like, what am I doing? Why am I doing this?” she said. Nathan Congleton/NBC via Getty Images

“I wanted to get people dating again! What are y’all doing if you’re not dating?” she said. “Love and be loved!”

The daytime reporter shares Hal, along with daughters Poppy, 11, and Mila, 13, with Henry. The couple tied the knot in May 2008 at her Texas family ranch.

Bush Hager has never shied away from talking about her former relationships and previously admitted she “didn’t date enough” before getting married during a 2024 episode of her morning show.

Jenna Bush Hager's children sit together at a kitchen counter for breakfast. — Bush Hager admitted she continued to entertain the conversation. jennabhager/Instagram

Jenna Bush Hager and her family pose outdoors. — Bush Hager shares three kids with her husband. (Seen here: The family of five.) jennabhager/Instagram

“I dated in college. I dated in high school. I didn’t date enough,” she told former co-host Hoda Kotb, who retired in January 2025.

“You don’t have to stay in a relationship if you are not engaged in it,” Bush Hager continued. “I was a serial monogamist, which was fine, but I should have dated more.”

The news anchor clarified that she and Henry had “built a really incredible life” that she is proud of, but advised women “should have fun and date” while they can.

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