Inside Jenna Bush Hager's Wild Past

Jenna Bush Hager isn't merely the offspring of a Hollywood star, forced to endure media scrutiny and public cajolery to follow in that parent's footsteps. One could argue it was even worse, as Jenna spent her early adult years living in a fishbowl called the White House, with father George W. Bush running the country. It also didn't help that their paternal grandfather, George H.W. Bush, was Ronald Reagan's vice president when the twins first checked in. "We were 'accidentally famous' from the moment we were born," wrote Jenna in "Sisters First: Stories from Our Wild and Wonderful Life," a memoir she co-wrote with her twin sibling, Barbara Bush.

And while Pops had to deal with fallout from 9/11, Jenna hardly stayed in the shadows. During her formative years, starting later in adolescence, she did what all her more obscure peers did best: get into lots of trouble. "I think [my father] really wanted Barbara and I to have normal childhoods," she said to Andy Cohen on a 2020 episode of "Watch What Happens Live." "And we did until he became president." While sister Barbara opted to head down a more obscure, straight and narrow path, Jenna took to the nightlife scene and became gossip fodder and a real headache for her protectors. Eventually, she settled down, but still retains a spirited disposition that hearkens all those wild years. Besides, she has a legacy of her own that rivals the exploits of other kids who grew up in the White House. 

"By the time my dad was in the White House, my luck with anonymity was gone," wrote Jenna Bush Hager in "Sisters First." It was an understatement that would haunt her early adulthood years. The media would have a field day with Jenna while attending college in Austin. Then 19, Jenna was arrested in April 2001 for underage drinking in a nightclub, where the legal age is 21. Two weeks later, Jenna landed into trouble once again, this time with sister Barbara Bush, who was visiting after finishing a year at Yale. The twins were busted for drinking booze in a restaurant, which led to Barbara getting probation. The court eventually nailed Jenna with a $100 fine, 36 hours of community service, and a Mothers Against Drunk Driving session. 

Going back to Washington, D.C. later that summer, Jenna was understandably scared over how her father, George W. Bush, would react. As she recalled on "Today," that moment of truth arrived when they went for a walk together. "'He said, 'I just want to talk to you about drinking," Jenna remembered her dad telling her. "'I found in my life it got in the way of things that mattered most, and I want to make sure that you just know that it can and be aware of it.'" That's when she discovered her teetotaling dad had a history of alcohol-related issues, and was even got nabbed for drunk driving in the '70s. 

By 2004, Jenna Bush already had a wild child reputation, one that skyrocketed while helping her father campaign to stay in the White House. While riding in a motorcade passing a gaggle of photographers in St. Louis, she playfully stuck out her tongue at the cameras. To no one's surprise, the gesture made front-page news. "I was with my dad and my sister, and I was, like, 'People don't even know what's going on in here, like watch this!' and Barbara and I constantly harassed [dad] and tried to make him laugh," Jenna recalled on "Watch What Happens Live" in 2020. But while working out in the hotel gym later that day, she feared she'd get a tongue-lashing from Pops after she saw her telltale visage beaming back at her from one of the TVs in the facility. 

Fearing a situation that could jeopardize her father's reelection prospects, she quickly left the gym and told him what happened. Instead, she faced what seemingly came across as more of an air of resignation about his daughter's playful personality. "Dad was just like, 'Jen, this is so typical," Jenna added. "You know, he thought it was, I mean, he thought it was funny." To this day, she still feels the tongue incident was blown out of proportion by the media. "What's wrong with that?" she said to KPRC (via Politico). "I loved that. I'll do it again."

Once Jenna Bush graduated from the University of Texas at Austin, she moved back to Washington, D.C. where she took to the city's nightlife scene like unconquered territory. Her after-hours dalliances, however, took place much to the chagrin of the Secret Service, who were in charge of protecting her. In his book "In the President's Secret Service: Behind the Scenes With Agents in the Line of Fire and the Presidents They Protect," former Washington Post reporter Ronald Kessler documented some frustrations the Secret Service experienced with Jenna who went to reckless extremes to evade her appointed guardians. "[Jenna] would sometimes purposely try to lose her protection by going through red lights or by jumping in her car without telling agents where she was going," wrote Kessler in the book.

Kessler also claimed that agents also had to quash a bar scuffle involving Jenna and her sister Barbara Bush, a situation that a press secretary for Laura Bush, the sisters' mother, dismissed as "nonsense." But Jenna recalled the Secret Service unwittingly became central to what she said was her worst date ever. That night, she went out with a lawyer named Henry Hager, who would eventually become her husband, when his car ran out of gas and started rolling down a hill backwards, colliding with a Secret Service vehicle tailing them. "He started to go up the hill and then boop, crash," Jenna said in People. "I was laughing, but he was horrified."

Once George W. Bush was inaugurated as president for the second time, Jenna Bush quickly became the toast of Washington, D.C.'s vibrant clubber scene, and regular grub for hungry society scribes. Home base for the imbibing shenanigans of Jenna and Barbara Bush turned out to be Smith Point, where budding young Republicans could cut loose. Jenna also became a regular with her boyfriend, Henry Hager, at The 9:30 Club, while Barbara dug the bar at The Jefferson Hotel. And even though Jenna and Barbara's inclusion in Washington Life Magazine's "The Young and the Guest List" summation of under-40 high-society types carried a certain cachet around town, other things written about Jenna weren't so flattering.

"Before there was the term 'fake news,' there was, well, fake news — snippets of outrageous stories that made the press or ended up on the Internet," wrote Jenna in "Sisters First." She discovered such scandalous allegations as going out with men she'd never met, that she was pregnant, and that she and Barbara dashed naked in a hotel in Mendoza, Argentina, a place she never visited. "I've learned to never Google myself," she added. Other items she believed were blown out of proportion, such as the time when the head of PETA was livid that Jenna had eaten foie gras in a restaurant. "Where did they come up with that?" she said to Texas Monthly. "The only meat I eat is fish."

Whenever someone runs loose on the grounds of the White House, the Secret Service treats it like a major security breach. But in one such instance that involved Jenna Bush, the results turned out to be something out of a movie. When Jenna finally became an item with Henry Hager — who had become an aide to Karl Rove, one of George W. Bush's advisors — a night of bar-hopping eventually led to 1600 Pennsylvania Avenue. "At one point, my parents were travelling and I was staying there," she said on "Today." "And we had gone out to the bars, and like all relationships do, they reached a certain level." She skipped the intimate details. The next morning, Hager freaked out that he was in the residence of Jenna's father, who was his employer. He frantically put on his clothes, rushed out of the bedroom, dashed out of the White House, and rattled the main gate to hail someone to let him leave the property. 

"Well, he was caught, that was the problem," said Jenna to Andy Cohen. "But as he says it ... they're supposed to keep people from coming in. They're not looking for people that are going out, especially like a 26-year-old, you know, in the night before a close." Fortunately, no charges were pressed. "[The Secret Service's] job wasn't to make sure I wasn't, you know, hooking up," Jenna added.

By 2006, Jenna Bush was turning off the tap on her party days, having landed a teaching job at a charter school and getting more serious about her relationship with boyfriend Henry Hager. But while assessing plans to teach in Latin America, she told Henry that he had a big decision to make. "When we were dating, I was leaving Washington D.C. and I kind of — in a dramatic fashion you may or may not recognize — said, 'If you don't want me to leave for Latin America, we need to get engaged,'" Jenna said on "Today" (via Us Weekly). "It was a manipulative ultimatum. Real manipulative." Later, they were to dine at a restaurant called Asia Nora where the staff customized the text for fortune cookies, but Henry was too late with his submission that was supposed to read, "Go and when you come back, I'll be here." Instead, they received two glasses of champagne, including one with a note that said "Don't go." In short, it was hardly a proposal.

The following year, Henry finally committed to the ceremonial knee-drop one morning when the couple were hiking in Maine. In 2008, the couple were married in a private, outdoor ceremony at the Bush ranch in Crawford, Texas. However, a few outlets were less congratulatory about the occasion, including Reuters which quipped, "Jenna has no great affinity for the press."

A young lady taking her grandfather out for a night at the movies might qualify for a Norman Rockwell caricature on the cover of the Saturday Evening Post, but in the case of Jenna Bush Hager, the scenario might have been more apt for a National Enquirer treatment. In 2009, she thought that her grandfather she lovingly called "Gampy" — better known to the country as George H.W. Bush, the 41st President of the United States — could use a few guffaws, so she suggested they take in a comedy flick. Except there was one problem: the film they caught was the Sacha Baron Cohen movie "Bruno," a mockumentary of a gay European fashion pundit that was loaded with nudity and expletives that were so graphic, Jenna recalled the accompanying Secret Service agents couldn't bear to look at the screen. "The worst part is, like, right away [Gampy] was like, 'Do we leave? Do we have to leave?'" she said to NBC cohort Willie Geist (via People).

But Jenna had much fonder memories of her grandfather, who passed away December 2018, seven months after his wife died. "Waking up missing this giant of a man who gave me everything," she wrote on Instagram. "He taught me and my family about service, family, decency, the power of gentle words and a beautiful heart. I will miss him desperately, but so happy he and my Grandmother are back together."

Fifteen years of marriage and mothering three kids hasn't been enough for Jenna Bush Hager to completely abandon her wild side. She's been known to make a few unfiltered comments from time to time, with co-host Hoda Kotb on "The Today Show," but fans really wanting to see the media personality fly her freak flag usually tune in for the Halloween episodes. That's when she's done everything from a twerking version of her grandmother Barbara Bush to a "Dirty Dancing" send-up. She was unrepentant about those outlandish portrayals, except for one. That exception would be the Halloween 2022 episode, when she impersonated her pop idol Celine Dion. "I need to apologize publicly to Celine, who I love," said Jenna to "Inside Edition" shortly after the episode wrap, which saw her belt out Dion's 1996 hit "It's All Coming Back To Me Now." "But I've been practicing that in my car since probably early 2002." While Jenna almost resembled the legendary singer in full regalia, she didn't have Dion's vocal range. But then, very few people do.

Still, it must be Jenna's favorite Dion classic. When she interviewed the vocal vanguard on "Today," Jenna reminded Dion about the time on a previous show in 2011 when they did an impromptu duet of the power ballad, before the footage of that momentous event started to roll. Cringing through that throwback, Dion exclaimed, "I cannot believe I did that!"

With all the past scandals and the stories she regularly shares, one might get the impression that Jenna Bush Hager is an open book. It turns out, however, there are still a few layers on her to be revealed, including one that "Today" co-host Hoda Kotb couldn't resist bringing to light in December, 2022. "Jenna never wears underwear," blurted Kotb before an astounded studio audience. 

After wails of protest that her big secret was made public, Jenna pointed out why she goes commando. "I think it makes a more pretty silhouette," responded Jenna with the audience reeling in laughter. "I also think you don't have to pack as much. There's a lot of pros to it. I'm sure my mom has never been more proud." A few weeks later, Jenna's 9-year-old daughter Mila Hager confirmed her mother's lack of attire. "She is not wearing it right now!" she added. "I saw her change!"

Medical advice website Healthline seems to be in Jenna's corner, pointing out a few advantages to going commando, including greater comfort, reducing the likelihood of yeast infections, and less exposure to materials that can cause allergic reactions. A 2014 poll by Vanity Fair and "60 Minutes" (via HuffPost) revealed that of 25% of respondents who said they don't wear underwear, 13% of them stated they doffed their drawers once weekly, while 7% revealed going commando all the time.

In 2009, Jenna Bush Hager joined NBC's "The Today Show" as a correspondent; 10 years later, she was selected to replace Kathie Lee Gifford as co-host for the show's fourth hour, alongside Hoda Kotb, and it's been tickety-boo ever since. Usually presented in a lighter and breezier format, the daily segment often sees the duo trade anecdotes of their personal lives, offer parenting tips, and even sample alcoholic beverages long before the bars open. But earlier in 2022, the well-lit set was eclipsed by a shadow of dissent on behalf of folks working on the show.

Apparently, NBC staffers were angry that Barbara Bush's twin sister was benefiting from a sideline gig of pitching Boll & Branch bed products, violating company rules. "NBC News has strict policies about endorsement deals and this kind of Bush League behavior," said an unidentified source who leaked the info to Radar. "It tarnishes the entire news division's credibility." One page dedicated to Jenna's picks on the Boll & Branch website shows the personality lying on a bed surrounded by pictures of sheets, pillow protectors, blankets and duvet sets. The page also offers a code word for patrons to access discounts and previously included a suggestive quote from Jenna: "My bed is a place I like to spend a lot of time. I wake up early, and I can't wait to get back in." Neither Jenna nor NBC has commented on the supposed controversy.