There Are So Many Weird Things About Jenna Bush Hager's Marriage

Jenna Bush Hager and her husband, Henry Chase Hager, have been together for two decades. Even if they were to split, that's already a successful relationship in our book. But that's not to say their marriage is picture-perfect in all aspects. On the contrary, there are plenty of weird things about it. It doesn't help that Jenna is an open book about her personal life. On "Today with Hoda & Jenna," the daughter of Laura and George W. Bush isn't afraid to overshare about her relationship.

Over the years, Jenna has revealed that she wished she had dated more people before she settled down with Henry. Despite not dating enough, Jenna kept mementos from the ones she did date, causing tension with her husband. Despite her preoccupation with the past, Jenna never hid her infatuation for him. She was so head over heels for Henry that she asked him to marry her just months into dating.

They didn't, and when she believed he was taking too long to pop the question, she tried to force him. That also didn't work. But they eventually married in May 2008, four years after meeting. Now, she feels so secure in her marriage that she's OK watching Henry flirt and be flirted with — it helps keep the spark alive. That's important after so many years together, when "the ick" factor begins to creep in — which it has for Jenna. All in all, Jenna and Henry have enjoyed a prosperous marriage, but it hasn't been free of weirdness.

When Jenna Bush Hager met her husband, Henry Chase Hager, in 2004, she was in her early 20s. That didn't leave her with enough time to play the field the way she would have liked. "I dated in college, I dated in high school. But I didn't date enough, which is what I realized," she said on "Today with Hoda and Jenna" in May 2024 (via People). While she is grateful for Henry, Jenna equates being settled with missing out on good times. "You should have fun and date while you can," she said. 

Jenna wants her children to learn from her mistake, seemingly displaying more concern for her daughters, Mila and Poppy, than her son, Hal. "Girls are taught that, 'Be careful or otherwise you'll get a bad reputation.' And you can do both. You can date a lot of people and stay true to yourself," she argued.

Jenna may not have dated as much as she would have liked, but that doesn't mean she didn't date quite a few people. In October 2024, Hoda Kotb gave her a hard time about running into Jenna's ex-boyfriends in Austin, Texas, home to the University of Texas, her alma mater. "Her prom date showed up at Don's the other night," Kotb said on "Today," adding they also ran into her 7th-grade date. Jenna didn't disagree. "It sounds like I still have a lot of exes that live in Texas," she said.

Jenna Bush Hager may be happily married to Henry Chase Hager, but she didn't see that as a reason to erase the guys who came before him. At least, she didn't until it became an issue. For years during her marriage, Jenna kept a box with mementos from her previous relationships. She never thought much about it, but Henry found the keepsakes and confronted her. "I was running from a meeting, and I get a text that says, 'I was looking for this old photo to frame, and I found your box,'" she said on "Today with Hoda & Jenna" in October 2024.

Jenna tried to brush it off, not seeing it as a big deal. "He said, 'Well, should we talk about it?' And I said, 'I don't think we need to,'" she revealed. However, she admitted she had a different reaction when she came across a box of older letters from Henry's exes. "I think I got rid of those," Jenna told Hoda Kotb. "I don't remember exactly." 

It's hard to say whose keepsakes Jenna was keeping in the box. Before tying the knot with Henry, she wasn't in any public relationships. But it's probably safe to say she wasn't keeping anything from the 7th-grade boyfriend who body-shamed her. "[He] broke up with me after we went swimming together after he saw me in a bathing suit," she told her co-host in an April 2024 "Today" episode. 

Jenna Bush Hager doesn't find everything about Henry Chase Hager attractive. Spending two decades with someone will do that, she told Justine Lupe when the "Nobody Wants This" actor shared she had never gotten "the ick" for someone she was in love with, referring to the sudden feeling of disgust for a partner brought on by a specific action. "Spoiler alert — because I've been with my husband for 20 years — you do get it," she said in a December 2024 episode of "Today with Hoda & Jenna."

She sees it as a normal occurrence and a nonissue. "There's so many more un-icks than icks," she added. The "Succession" star wasn't going to let Jenna off the hook that easily, though. "What is one of his icks?" she asked. Jenna drew a breath to answer, but Hoda Kotb jumped in before she could. "No, no, don't. Don't!" she said. "Because you know what happens, Justine? It gets in Page Six, and she gets in trouble. I'm protecting her from herself."

This wasn't the first time Jenna and Kotb discussed the ick factor on their show. During a February 2024 episode, Jenna argued that once you're in a marriage, you have to work hard to keep those feelings at bay. "You got to push those icks right out of your brain," she told the audience. She admitted it's not always easy. "It's going to be ick after ick after ick." 

Jenna Bush Hager felt so strongly that Henry Chase Hager was the one that she proposed to him three months into the relationship. "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?'" she recalled on "Today with Hoda & Jenna" in 2020. But Henry preferred a more pragmatic approach. "He smiled, and he was like, 'I'm crazy about you, but you're young,'" she shared.

Henry proved he was in no rush to tie the knot, though. Years went by, and Jenna's ring finger remained bare. Tired of the wait, Jenna gave her now-husband an engagement ultimatum — but it didn't go as planned. When she was ready to leave Washington, D.C., she threatened to move to Latin America unless they got engaged. She thought her attempt at manipulation had worked because, shortly after, Henry arranged a romantic dinner at a restaurant.

When the waiter brought out two glasses of champagne with a custom-made fortune tied around one that read "Don't go," Jenna said "Yes" to what she thought was a proposal. However, the restaurant got the message wrong. Henry had intended it to be something like: "Go, and when you come back, I'll be here." Henry was mortified. "His face dropped. He could've cried," she told Hoda Kotb in a 2023 "Today" episode. Henry proposed for real in 2007, three years into their relationship. 

Many people find it disrespectful when others come on to their significant other, but Jenna Bush Hager isn't one of them. For the most part, she gets a kick out of watching women make romantic advances to Henry Chase Hager. "This may be weird, but sometimes I like it when people flirt with Henry," she said on "Today with Hoda & Jenna" in March 2024. After Hoda Kotb pressed her, she explained that it made her feel special. "I don't know. I'm just like, 'Oh, baby girl's still got it,'" she said.

To Jenna, her feelings are a sign of the health of her marriage. "I'm very secure in our relationship. So I'm like, 'Oh, there you are,'" she quipped. She's so confident in what she and Henry have that she doesn't even mind if he flirts back. "If it's a very small amount, I find it attractive. He wouldn't do it a lot," she told Kotb. However, she admitted that her husband has very little opportunity to flirt or be flirted with. "We don't really go anywhere," she said, a statement that parents everywhere can surely nod in understanding.

As parents to three children, Jenna and Henry find little time to mingle. But, as a homebody, she doesn't seem to mind. "Since Henry and I both have big jobs, I'm hoping that our kids realize the biggest job and the biggest priority is them," she told People in 2019.