A Timeline of Jenna Bush Hager and Henry Hager’s Relationship

Jenna Bush Hager often finds herself emotional as she reflects on the enchanting love story she shares with her husband, Henry Chase Hager.

“I truly feel fortunate to have found someone who has blessed me with three wonderful little kids,” she expressed regarding their family during the fourth hour of TODAY in May 2024. “We’ve built a life together, and I’m incredibly proud of what we’ve achieved.”

According to Jenna, the key to their enduring marriage is their mutual growth and evolution as a couple over the years.

“Henry is simply the best,” she remarked. “He has introduced me to so many things I now love. Being an Eagle Scout, he loves hiking, and we engage in a variety of adventures together. What’s fantastic is how we both are eager to explore new things; he never says, ‘Oh, I don’t want to see that show or do this.’ He’s open-minded, and that’s truly enjoyable.”

Jenna and Henry’s bond has lasted nearly two decades.

The initial spark between them ignited in 2004, while Henry was employed by Jenna’s father, former President George W. Bush.

Jenna quickly realized Henry was the one for her, leading to their beautiful history together.

Today, they are parents to three children, and Jenna frequently shares insights into their family life as a quintet on her Instagram.

Here’s an overview of Jenna and Henry’s relationship journey over the years.

Jenna met Henry when he worked on former President George W. Bush’s campaign in 2004

Jenna was introduced to Henry by mutual friends while he worked on the 2004 reelection campaign for her father.

“He was working for my dad,” Jenna recounted on the fourth hour of TODAY in 2019. “A college friend of mine was his intern, and during a Texas game watch party, they asked, ‘Can we bring Henry along?’”

Years later, Jenna shared a nostalgic photo on her Instagram story featuring the first picture taken with Henry, which was from December 2004 when she was 23 and he was 26.

“We’ve been together for a million years,” she humorously noted in the caption.

The couple experienced a memorable first date involving the Secret Service

As the daughter of a president, Jenna faced unique dating challenges, including the watchful eye of the Secret Service.

She recalled an awkward incident where Henry inadvertently crashed into a Secret Service vehicle in Arlington, Virginia, while searching for gas with a dwindling fuel tank.

“Let’s just say my worst first date involved the Secret Service,” Jenna revealed on the fourth hour of TODAY in 2021. “Henry’s car ran out of gas, rolled backward, and hit the Secret Service.”

“Were you scared or laughing?” her co-host Hoda Kotb inquired.

“I laughed, but he was mortified,” Jenna recollected.

Henry made a stealthy exit from the White House ‘walking as fast as he could’

At one point during their dating phase, Jenna said Henry had to sneak out of the White House the morning after their relationship escalated to “another level.”

“Henry said he woke up and looked around, thinking, ‘Aaaaaaaah,’ since he worked for my dad,” Jenna chuckled on the fourth hour of TODAY in 2022.

She explained that Henry was “walking as fast as he could” to avoid detection while trying to maintain composure.

“He described escaping the White House as equally challenging as entering it,” Jenna added. “The guards are always on the lookout for anyone running out.”

Jenna humorously remarked that Henry was still in his clothes from the previous night as he tugged at the gate.

When sharing this amusing story on TODAY, Jenna mentioned it was the first time she revealed this to her parents.

“Do you think they’ll find it amusing? I mean, I’m almost 41, and we have three kids!” she remarked.

Jenna recognized early on that Henry was ‘the one’: ‘I could be my true self’

Jenna realized Henry was the ideal partner for her quite early.

“One reason I quickly understood Henry was ‘the one’ is that I could entirely be myself without pretenses, and he embraced that,” she told Hoda on TODAY in 2020.

She explained that with previous partners, she had feigned interests to make an impression—like telling a high school boyfriend she was an avid skier, although she’d never skied before.

“Then Christmas came, and he invited me to join his family on a ski trip!” she recounted about her little fib. “I went to my parents and told them ‘Mom and Dad’ … it caught up with me.”

But with Henry, she felt comfortable being genuine.

“At a certain point, you just are who you are, right?” she reflected.

Jenna proposed to Henry first, only months into their relationship: ‘What’s stopping us?’

Convinced of her feelings early on, Jenna proposed to Henry just three months into dating.

“After three months, I may have had a holiday cocktail, and while we danced, I said, ‘This is it; I know it, let’s get married right now; what are we waiting for?’” Jenna recounted on TODAY in February 2020.

“He smiled and said, ‘I’m crazy about you, but you’re still young,’” she added.

In August 2023, Jenna elaborated on that moment, mentioning her sister Barbara was present while it happened.

“I was 22 at the time, and Barbara was there, and as we danced, she started shuffling backward, wondering, ‘What’s happening here?’”

She reminisced that Henry expressed his love for her as well, and she declared, “‘Me too: Let’s get married!’”

However, Henry didn’t fully accept her lighthearted proposal initially.

“He said no, but then we tied the knot five years later,” Jenna recalled. “He didn’t say no; he just chuckled.”

Henry sought the president’s blessing to marry Jenna in 2007

In 2007, Henry requested Jenna’s father’s blessing during a Fourth of July family retreat at Camp David, Maryland.

Henry was visibly anxious about asking the president for permission, going so far as to “read the Bible” for guidance, Jenna shared with TODAY guest host Justin Sylvester in August 2023.

To add to the tension, Henry struggled to find an appropriate time to speak privately with the president.

“He called my dad to set up a meeting, and my dad replied he was taking a nap and could only meet a few hours later,” Jenna explained to TODAY. “So Henry had to fret while waiting.”

Once Henry finally got the chance to chat with Jenna’s father, he came prepared.

“He had crafted a seven-point plan on why he wished to marry me and how he would take care of me. My dad interrupted and said, ‘Henry, I already said yes; you don’t need to present anything else,’” Jenna recalled, adding that her father then informed her mother, former first lady Laura Bush: “‘Laura, Henry’s proposing,’ and that concluded it. Thankfully, he did it.”

Jenna and Henry married in 2008

Jenna married Henry on May 10, 2008, at her parents’ Prairie Chapel Ranch in Crawford, Texas.

She fondly remembers a touching moment with her father on their wedding day.

“Dad picked me up in his pickup truck, looked at me and said, ‘You look beautiful, baby,’ and then we both cried,” she shared on the fourth hour of TODAY in 2021.

Additionally, on their wedding day, Henry stood at a cross that her father helped build.

“It’s still standing, and we hold our family Christmas services there, and our kids have had the chance to stand on it,” she added.

The couple welcomed their first child, Mila, in 2013

Their first child, Margaret Laura “Mila” Hager, was born on April 13, 2013.

Mila’s name pays tribute to both of her grandmothers: Laura Bush and Henry’s mother, Margaret.

Baby Mila was actually due in May but arrived early after Jenna went into labor during her baby shower.

“I felt what felt like my belly going ‘blop blop,’ and someone said, ‘Girl, you’re going to have that baby right now.’ Then it was like, three, two… water break,” Jenna recounted on TODAY in April 2023.

Henry went into “panic mode” upon hearing that Jenna’s water had broken—initially thinking it was a prank.

“Henry thought we were joking, thanks to Barbara and me teaming up against him,” Jenna remarked.

The couple welcomed their second daughter, Poppy, in 2015

Their second daughter, Poppy Louise Hager, was born on Aug. 13, 2015.

Poppy’s name is inspired by Jenna’s grandfather, former President George H.W. Bush, who was affectionately known as Poppy.

“We are so proud to name her after someone we cherish so much,” Henry said on TODAY in 2015.

Additionally, Henry mentioned that Poppy’s middle name pays homage to both of their grandmothers—Louise and Lewis.

The couple’s third child, Hal, was born in 2019

Jenna and Henry welcomed their first son, Henry Harold “Hal” Hager, on Aug. 2, 2019.

On Hal’s fourth birthday, Jenna shared his birth story on TODAY.

She revealed that she was not able to indulge in celebratory treats right away post-birth due to having a C-section.

“After having Hal for an hour, my sister brought tacos and doughnuts, but the nurse informed me I couldn’t have them,” Jenna told Hoda, adding that she told Hal about the details of his birth.

“I FaceTimed him this morning and said, ‘Hal, did you know that just an hour ago, four years ago, you were cut out of my tummy?’” Jenna shared on TODAY.

Hal seemed surprised by the revelation.

“He exclaimed, ‘Cut out of your tummy?’” Jenna said.

“You’re so literal,” Hoda replied with laughter.

Henry played a hilarious prank for Jenna’s 40th birthday on TODAY

When Jenna turned 40 in 2021, Henry surprised her with an unforgettable on-air moment.

To celebrate his wife’s milestone birthday,henry disguised himself as an NBC page and queried strangers about their knowledge of Jenna, including their guesses on her age.

One individual guessed she was 32, while another scolded Henry for inquiring about a lady’s age.

“That was a challenge,” Henry remarked after his stint as an NBC page. “I’m off to get a coffee and warm up; I won’t attempt this again.”

He then added a heartfelt message for his wife.

“Jenna, you’re an incredible anchor. You excel at your job,” he stated. “I’m in awe of how you manage it. I love you. Happy birthday!”

They celebrated their 15th anniversary: ‘I adore him. A lot.’

In May 2023, Jenna commemorated their 15th anniversary with a heartfelt Instagram post.

She included wedding day photos, along with a candid shot of her and Henry on the subway, and another heartwarming picture of them smiling on a boat ride.

“15 years with HH by my side,” she wrote in her caption. “I adore him. A lot.”

Jenna shared Henry’s thoughtful gesture during the pandemic: ‘It’s the little things’

On the fourth hour of TODAY in March 2024, Jenna reminisced about how Henry surprised her with a sweet gesture during the COVID-19 pandemic.

“During COVID, some days felt endless: hosting the show from our kitchen, feeling isolated, juggling kids’ Zoom calls, and cooking yet again,” Jenna shared with Hoda.

But then, Jenna walked into her bedroom to discover a candle lit and a heartfelt letter from her husband.

“I walked into our room, and Henry had lit a candle, that was it, along with a beautiful letter about how, despite the fear and uncertainty, there was no one else he’d prefer to navigate this with,” Jenna added.

At this, Hoda let out a surprised laugh, wiping away tears from the emotional moment.

Jenna explained that she interpreted Henry’s gesture as an invitation to “lay down and relax.”

“‘I see you, and I know you’re exhausted and taking on a lot, so just take a moment to relax,’” Jenna described his message. “It is the little things that matter, right?”

“That’s such a lovely sentiment, and it’s a small, meaningful gesture,” Hoda responded.

Jenna celebrated Henry’s 46th birthday and their 16th anniversary

Jenna commemorated Henry’s 46th birthday on Instagram on May 9, 2024, sharing a series of family photos.

She wrote, “Happy birthday to the best who is not into social media! Henry Hager, we ❤️ you deeply! We’ve celebrated 20 birthdays together…..(still feel 26!!).”

Among her sweet wording, Jenna posted 10 photos featuring Henry.

In the first picture, the couple takes a mirror selfie with their daughters Mila and Poppy in Taylor Swift apparel. Other images capture Henry smiling alongside Jenna and interacting with their son Hal.

The couple also observed their 16th wedding anniversary on May 10, 2024.

Jenna reflected on their love story during the May 10 episode of the fourth hour of TODAY, expressing her sense of “luck” to be married to Henry and to share “three wonderful little kids” with him.

“We’ve established a life together, and I’m immensely proud of both of us,” she concluded.

Jenna admires Henry’s parenting style

In June 2024, Jenna praised a sweet gesture that Henry performed for their daughters, Poppy and Mila.

She shared how he took the girls to support the Washington Spirit, a professional women’s soccer team based in Washington, D.C.

The girls also got the opportunity to participate in a players’ huddle before the game, which the Spirit won.

“I’m thrilled to be married to a man who truly loves women’s sports. He cherishes it enough to drive an hour and a half for a game at 6 p.m. along with the kids,” Jenna noted during the fourth hour of TODAY. “To huddle up with these amazing women was a fantastic experience.”

In August 2024, she shared another story about how Henry assisted their kids in starting an ice cream stand, teaching them about entrepreneurship and philanthropy.

They had visited an ice cream shop in Martha’s Vineyard when Henry exclaimed, ‘This place is so pricey — watch me!’” Jenna recounted to Hoda.

For their kids to grasp the concept of finances, Henry took them to a grocery store to purchase the same amount of ice cream cartons. They later sold the scoops at their ice cream stand and donated the earnings to charity.

Last summer, Jenna also described how Henry responded to their daughter Mila’s request for a debit card tailored for kids.

Initially, both Jenna and Henry were against the idea, but Mila impressed them with her responsible reasoning.

“She created a PowerPoint presentation … outlining why she was now responsible enough and what chores she would take on, plus her desire to save up money to buy Christmas gifts for her siblings on her own—she wanted to handle that without our help,” Jenna told Hoda.

Ultimately, even Henry was convinced to give it a shot.

“Henry, who usually spends cautiously, agreed, ‘Alright, Mila. You’ve earned it,’” Jenna confirmed. “She accomplished this independently.”

The couple treasures joyful moments during the holiday season

In November 2024, Jenna posted photos of Henry and their kids celebrating her 43rd birthday on Instagram.

One photo captures Henry and the kids joyfully holding her birthday cupcakes, while another features a more candid moment with Hal, then 5, experiencing “a little meltdown.”

“Feeling incredibly grateful for all the love… truly savoring every moment,” Jenna wrote in her caption. “As someone advised me today, I hope to slow down a bit to fully appreciate every single second. Thank you for everything.”

Later that month, she shared additional pictures with Henry and their kids during Thanksgiving on Nov. 29.

She encapsulated her feelings about the day in just one word in the caption: “GRATEFUL.”

The following month, she once more celebrated her family of five, showcasing their playful sense of humor in their annual holiday card.

One of the holiday card images captures Jenna, Henry, and the kids posing lovingly by a wooded area, while another shows them dressed in whimsical fairy-tale costumes.

Jenna and Henry fully embraced their roles, complete with powdered wigs and 18th-century attire.

Jenna shared another Instagram post featuring their family of five on Jan. 1, 2025. In a brief video, Henry holds Hal while Jenna stands with their daughters, who are dressed in festive sequined outfits.

“2025, we’re ready!” Jenna wrote in her caption.