Hoda Kotb and Jenna Bush Hager Share Their Biggest Dating Regrets: ‘I Should Have Dated More’

Hoda Kotb and Today cohost Jenna Bush Hager had a candid conversation about their biggest regrets when it comes to dating.

During an episode of the talk show on Thursday, May 23, Hoda, 59, admitted that she often second guessed herself while dating men in the past.

“One of the things I used to want when I met someone was, ‘Does he like me? I so hope he likes me,'” she said. “Not, like, ‘This is who I am.’”

“You can be the juiciest orange in the bunch, but some people don’t like oranges. I can’t help you if you don’t like oranges, I’m that,” the Hope Is a Rainbow author continued.

Take a Tour of Jenna Bush Hager's Extravagant Long Island Home

Ultimately, Hoda learned a huge lesson about finding self confidence and embracing who she is. The broadcaster was married once to Burzis Kanga from 2005 to 2008. She was in a relationship with ex-fiancé Joel Schiffman from 2013 to 2022. They share daughters Haley and Hope.

Hoda returned to the dating scene after her split from Joel with a new perspective.

“Something did happen the other day that hasn’t happened in two years. I had a date. I had a date,” she said during an appearance on The Kelly Clarkson Show on March 5. “You know what it was? Just a date. It was nothing but a date.”

As for Jenna’s love life, she’s been happily married to her husband, Henry Hager, since 2008. They welcomed kids Mila, Poppy and Hal. And while the former first daughter is thankful she found the right person, she made a major confession during the Today episode.

“I dated in college, I dated in high school. But I didn’t date enough, which is what I realized,” Jenna, 42, told Hoda.

“I want to talk to my kids, not only [to give them] the Tracee Ellis Ross [advice of] ‘You’re the chooser’ but [also to tell them], ‘You don’t have to stay in a relationship if you’re not engaged in it.’ Like, I was a serial monogamist, which was fine,” she added. “But I should have dated more.”

Jenna met Henry when he was working for her father, former President George W. Bush, during his 2004 reelection campaign.

“I met the right person early and it’s great and we’ve built a really incredible life and I’m proud of it,” the mom of three explained. “But also, you should have fun and date while you can.”