Jenna Bush Hager Thinks She 'Should Have Dated More' Before Settling Down With Husband Henry Hager

'Today's Jenna Bush Hager married Henry Chase Hager in 2008. They share two daughters -- Mila, 11, and Poppy, 8 -- and son, Hal, 4.

Jenna Bush Hager feels like she "didn't date enough" before settling down with Henry Chase Hager.

The 42-year-old Today show personality made the revelation on Thursday after sharing with co-anchor Hoda Kotb that the 22nd (or 23rd, Hager couldn't exactly recall) anniversary of meeting her now-husband is coming up in September. That prompted Hoda to wonder if Jenna dated much before tying the knot in 2008.

"I dated in college. I dated in high school. I didn't date enough," Jenna admitted, to which Hoda responded with, "Oh, that's interesting."

Jenna added she wanted to impart wisdom on her kids, "You don't have to stay in a relationship if you are not engaged in it. I was a serial monogamist, which was fine, but I should have dated more."

When asked why, Jenna prefaced her answer by saying she's glad she met "the right person" in Henry, but looking back she wishes she would have taken a different approach.

Jenna Bush Hager and Henry Hager attend The George H.W. Bush Points of Light Awards Gala on Sept. 26, 2019 in New York City. - Getty

"We have built a really incredible life and I am proud of it," said Jenna of her marriage to Henry and being parents to three children -- daughters Mila, 11, and Poppy, 8, and son, Hal, 4. "But you should have fun and date while you can. I think girls are taught, you know, be careful because otherwise you will get a bad reputation. You can do both. You can date a lot of people and stay true to yourself."

Jenna said that being committed to monogamous relationships is rooted in how she viewed romance as a young girl.

"You had this dream of the prince," she said. "Therefore, I went into relationships -- if I'm honest -- thinking is this one going the distance?"

Jenna and Henry tied the knot in May 2008 after a four-year courtship. Henry worked as Staff Assistant to the Senior Advisor at the White House to Jenna's dad, President George W. Bush, from 2001 to 2003. Henry then worked on his reelection campaign as Deputy Operations manager before serving positions in the U.S. Department of Commerce. It was during George W.'s second-term that Jenna met Henry. They got engaged in 2007.

It's not the first time Jenna has talked about Henry on Today. In March, she admitted to "sometimes" liking it when people flirt with her husband. Confused, Hoda asked, "Why?"

"I don't know, it's just like, 'Oh, baby girl's still got it!' Because I know I'm very secure in our relationship," she said of her marriage of over 15 years. "I'm like, 'Oh, there you are!'" 

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