Unraveling the Quirky Aspects of Jenna Bush Hager’s Marriage

Jenna Bush Hager and her husband, Henry Chase Hager, celebrate two decades of togetherness, marking what many would view as a success. However, their marriage, while stable, has its quirks. Jenna, known for her candidness on “Today with Hoda & Jenna,” often shares details about her relationship, revealing both the good and the peculiar.

Throughout the years, Jenna has expressed a desire to have dated more before committing to Henry. This has led to some disputes, especially since she kept tokens from her past relationships. Despite her reflections on past romances, her love for Henry has always been evident; she famously proposed to him just a few months into their relationship.

When Henry took what felt like an eternity to propose, Jenna attempted to push him into it, though that plan also failed. They eventually tied the knot in May 2008, four years after they first met. Today, Jenna feels confident enough in their bond to not mind if Henry flirts or receives attention from others—she believes it keeps their long-term relationship vibrant. After many years, they still navigate the complexities of maintaining intimacy, acknowledging the “ick” factor that sometimes arises.

When Jenna first met Henry in 2004, she was still in her early twenties and had insufficient time to explore various relationships. Reflecting on her past, she mentioned on “Today with Hoda and Jenna” that while she did date during high school and college, she wished she had dated more extensively before settling down. Jenna carries a sense of gratitude for Henry but feels settling down may have robbed her of more adventurous experiences.

Concerned for her daughters, Mila and Poppy, Jenna hopes they learn to balance freedom in dating with maintaining their integrity, noting that societal pressures often restrict young women. Jenna gently encourages them to embrace opportunities while staying true to themselves.

While Jenna may not have dated as much as she desired, she’s had her fair share of relationships. In October 2024, her co-host Hoda Kotb joked about the numerous ex-boyfriends Jenna has encountered in Austin, Texas, where they stumbled upon her prom date and even a 7th-grade date. Jenna humorously acknowledged this, suggesting that she still has plenty of former flames in Texas.

Although Jenna is happily married to Henry, she has not felt the need to discard memories of her previous relationships. This attitude came to a head when Henry discovered a box of sentimental items from her past. In a moment of surprise, he texted her after finding the box, which prompted a discussion between them.

Jenna downplayed the situation, initially viewing the box as unimportant. However, she confessed that she reacted differently upon finding Henry’s old letters from his own ex-girlfriends, suggesting a double standard. While the specifics of what she kept remain unclear, it’s likely not from a significant public relationship prior to Henry’s.

Sharing a funny anecdote, Jenna recalled how a childhood boyfriend ended their relationship after criticizing her appearance in a swimsuit, indicating that her past experiences have shaped her perspective today.