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Jason Segel just revealed how his fiancée Kayla Radomski utterly “lost it” during their elaborate surprise proposal. The Shrinking star, 46, shared intimate details about orchestrating the perfect garden moment that had his then-girlfriend sobbing with joy.
🔥 Quick Facts
- Proposal Date: June 16, 2025, at Huntington Gardens in San Marino, California
- Engagement Announced: June 18, 2025 via Instagram by Kayla Radomski
- Interview Details: April 8, 2026 appearance on Jimmy Kimmel Live with full proposal backstory
- Ring Designer: Jason Segel designed the custom engagement ring himself
How Jason Orchestrated the Ultimate Surprise
The How I Met Your Mother star carefully crafted an elaborate deception. Segel told his girlfriend that they couldn’t get engaged until Shrinking wrapped. The show was “very overwhelming,” he explained, buying precious time to plan.
Then came the fake story. Segel invented a fictional “donor dinner” at Huntington Gardens, the botanical gardens where they’d gone on an early date. “As time went on, I really couldn’t hold this lie very well,” he admitted on late-night television. He kept adding details, claiming the mayor would attend and that the LA Times would cover the event. The escalating deception made the evening sound “like a total chore,” Segel recalled with a laugh.
Jason Segel reveals how fiancée Kayla ‘lost it’ during surprise garden proposal
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The garden staff played along perfectly, welcoming the couple to the fake after-hours gala. When Radomski spotted a carpet lined with rose petals, she assumed it was for another couple. “Aw, someone must have just gotten married here,” she told Segel.
The Golden Moment That Made Her ‘Lose It’
Standing near a Greek statue, Segel guided his unsuspecting girlfriend through a simple ritual. “I said, ‘Yeah, this is the love statue. Close your eyes, make a wish,'” he explained. While both had their eyes shut, Segel dropped to one knee and proposed.
Initially, Segel thought he’d missed his main goal. He wanted to make Kayla “cry real hard” and saw only a single tear. “This is not enough crying,” he thought to himself. But then the string quartet began playing “Tale as Old as Time” from Beauty and the Beast, her favorite movie, and everything changed.
| Detail | Information |
| Proposal Location | Huntington Gardens, San Marino, California |
| Significance | Site of couple’s first romantic date |
| Song Played | “Tale as Old as Time” from Beauty and the Beast |
| Ring Design | Custom, designed by Jason Segel |
“She lost it.” Jason Segel on Kayla’s reaction when the string quartet began playing her favorite song
A Ring That Captured Her Spirit
Segel revealed his thoughtful design philosophy for the engagement ring. “Kayla’s this amazing mix. She presents as a Disney princess, but she’s a total weirdo,” he explained. The actor set out to create something reflecting her unique personality combination.
He personally designed the custom ring to capture both her elegance and her quirky, unfiltered nature. The result was a piece that felt uniquely hers, matching the thoughtfulness Segel brought to every detail of the surprise.
The Relationship That Changed Everything
Segel and Radomski announced their engagement on June 18, 2025, through an Instagram post from the dancer. The couple had dated for nearly two years after going public at the Golden Globes in early 2024. The 46-year-old actor confirmed that his friend, disguised as a tree, hid in the bushes to capture photos of the magical moment.
Most recently, the couple celebrated their engagement with a party at Cannonball restaurant in South Pasadena in January. Segel gushed about his fiancée, saying his entire life perspective has shifted. “My whole life, work has been my beloved, and now the whole lens of how I view things has switched and I’m having the best time of my life,” he told Jimmy Kimmel.
Will Jason Segel’s Engagement Story Inspire Your Own Proposal Plans?
The Forgetting Sarah Marshall star has set an extraordinarily high bar for romantic proposals. His meticulous planning, emotional connection to the venue, and personalized details suggest that Segel treated the engagement with the same care he brings to his acting craft.
For fans of Jason Segel, watching him gush about Kayla Radomski on late night television proved he’s discovered something far more fulfilling than Hollywood accolades. The question now becomes, as wedding planning begins, what creative surprises await next for this fairy tale couple?
Sources
- People.com – Jason Segel’s Jimmy Kimmel Live interview revealing engagement proposal details and ring design philosophy
- Yahoo Entertainment – Behind-the-scenes account of elaborate lies and surprise elements orchestrated for the proposal
- E! Online – Coverage of the June 2025 engagement announcement and two-year dating timeline
