Jenna Bush Hager Dishes on Her Worst First Date Ever With Husband Henry Hager

From Good Housekeeping

In February 2005, reporters asked former First Lady Laura Bush about a guy her daughter Jenna had been dating. Was he the one? At the time, Laura declared that she didn't see him as "a serious boyfriend." But as it turns out, she was dead wrong.

That "guy" is Henry Chase Hager – the son of former lieutenant governor of Virginia John H. Hager and the Today show star's husband of 12 years now. Today, they have three kids: Mila, 7, Poppy, 5, Henry Harold "Hal" Hager, 1.

It's crazy to think that over 15 years ago, Jenna and Henry were just meeting for the very first time.

The President's daughter is introduced to her father's employee

Jenna had recently graduated from the University of Texas and started teaching at Elsie Whitlow Stokes Community Freedom Public Charter School in D.C. Meanwhile, Henry, who had been a student at the University of Virginia's Darden School of Business, was busy working for former President George W. Bush's 2004 re-election campaign.

It was on the campaign trail that the two crossed paths. Jenna revealed on Today that Henry had a girlfriend at the time, though. But after he came over to watch a Texas football game, that was it. As one of Henry's friends disclosed to People back in 2008, “On Election Day, they were friends. By the Inaugural, they were an item.”

Most recently, Jenna opened up to her fellow Today show cohost Hoda Kotb about her first date with Henry, which didn’t exactly go as planned.

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

She elaborated that at the time he was living in Arlington, Virginia, and on their first night out, Henry realized that he was running low on fuel. But while driving to a corner gas station, they ran into an unexpected problem.

“He started to go up the hill and then booooop, crash,” she said. “I was laughing but he was horrified.”

According to The Washington Post, the two quickly became inseparable. Inaugural parties, the White House Dinner, and other public events — whenever they could be together, they were. In fact, Jenna revealed on the Today show that she was so sure Henry was the one, she proposed to him after only a few months of dating.

"He said no ..." Jenna told her costar Hoda before telling the full story.

"I might've had a Christmas cocktail — and we were dancing, and I said, 'This is it, I know it, let's just get married, what are we waiting for?' He smiled, and he was like, 'I'm crazy about you, but you're young.'"

A fake-out proposal and asking for permission

When May 2006 rolled around, Jenna was still more than ready to say "yes." As she spilled to CultureMap Dallas in 2018, Jenna thought Henry was proposing when the two went out to dinner one night at Asia Nora in Washington D.C. When waiters came around with a bottle of champagne with a note on it, Jenna took the note off, read it, and, apparently, started laughing hysterically.

"I thought you were proposing!" she yelled loud enough for everyone to hear. "I nearly [soiled] my pants!"

Photo credit: Getty
Photo credit: Getty

Alas, it wasn't a proposal. But rest assured, when Henry did pop the question in August 2007, he had already asked for her dad's permission.

"So the guy comes to see me, and he says, 'I want to marry your daughter,'" the 43rd President allegedly recalled. "I said, 'Done deal.'"

In terms of how he proposed, The Knot reports that Henry took his future bride on a vacation in Maine. One morning, he woke Jenna up at 4 a.m. to go on a hike to Cadillac Mountain in Acadia National Park. Timing it perfectly, they reached the top of the mountain when the sun was rising. Right then and there, Henry asked Jenna if she would be his wife forever.

A romantic Texas wedding

On May 10, 2008, Jenna and Henry walked down the aisle at the Bush's secluded ranch in Crawford, Texas — the same day as the groom's 30th birthday. At the event, George and Jenna twirled around the dance floor to "You Are So Beautiful."

Photo credit: Getty
Photo credit: Getty

After the wedding, the President said at a press conference, "Our little girl, Jenna, married a really good guy."

Photo credit: Getty
Photo credit: Getty

When marrying Henry, Jenna explained why it was an easy decision for her to take his last name. “I never debated,” she said on the Today show. “I love my family, but it’s nice to have your own name too.”

Kids, new jobs, and balancing it all

One year after they got married, Jenna joined Today as a national correspondent, which led to an anchor position. In the spring of 2019, she replaced Kathie Lee Gifford in the show's fourth hour (KLG's last day was on April 5).

While so much has happened over the course of their relationship, Jenna seems to be just as in love with Henry now as she was back then — if not more.

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“Your love is like the Post-it note with stick figure drawings of ships passing that you left for me on the bathroom mirror when I returned home late. I'd been flying most of the day and I was dehydrated, and thirsty for home, for you,” she shared on the Today show. “Your love is like that note. It is simple and solid and thoughtful."

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