He wasn’t just pulling up for a first date—he was about to make federal history.
What began as a casual evening out between two young romantics quickly veered into full-blown political farce, complete with a stalled engine, a rogue hill, and a very unhappy Secret Service agent. For Jenna Bush Hager and Henry Hager, their early romance came with high stakes—and even higher comedy.
“Henry woke up the next morning, looked around, and literally screamed,” Jenna laughed, recalling the moment with vivid delight. “I mean, he worked for my dad. And I just told him, ‘Have fun with that—I’m out!’”
The real kicker? This wasn’t some tabloid exaggeration—it happened. During what Jenna describes as her worst first date ever, the car ran out of gas at precisely the wrong moment.
“We were heading uphill when he suddenly realized we were running on fumes,” she told People. “He tried to make it to the gas station, but instead, the car just gave up—rolled backward down the hill and crashed right into the Secret Service car following us.”
That’s right: their unassuming date night ended with a full-on fender bender… with federal agents.
“I was dying laughing,” Jenna recalled. “But Henry? He was mortified.”
conlusion:
What could have been a relationship-ending disaster instead turned into one of the most memorable footnotes in their love story.
From rolling into Secret Service vehicles to rolling with life’s punches, Jenna and Henry Hager’s early days were full of surprises, mishaps, and a fair bit of secondhand embarrassment. But their ability to laugh through the awkwardness proved to be the glue that stuck—and stuck hard. Because sometimes, the best stories begin with a crash… literally.