Jason Segel Reveals the Moment His Fiancée Kayla Radomski 'Lost It' During Surprise Proposal

Ashlyn RobinetteThu, April 9, 2026 at 5:53 PM UTC

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Kayla Radomski and Jason Segel in September 2025Credit: Francis Specker/CBS via Getty -

Jason Segel and Kayla Radomski announced their engagement on June 18, 2025

The actor opened up about his garden proposal during his recent appearance on Jimmy Kimmel Live!

Segel staged an elaborate surprise, including a fake "donor dinner" and a string quartet playing a song from Radomski's favorite movie

Jason Segel is opening up about his engagement to Kayla Radomski.

During his appearance on Jimmy Kimmel Live! on Monday, April 6, the Shrinking star, 46, spoke about his elaborate surprise proposal to his fiancée, 35, and revealed the moment she "lost it."

"My measure of this, if I had done it right, was if she burst into tears, which is a high mark," Segel told host Jimmy Kimmel, 58. "I wanted her to cry real hard. I wanted it to be the best moment of her life."

Jason Segel on 'Jimmy Kimmel Live!'Credit: Jimmy Kimmel Live/YouTube

Segel popped the question at Huntington Gardens in California, which is a sentimental spot to the couple because they had an "early date" there. Ahead of the proposal, Segel threw off any suspicion by going into "full acting" mode. He first told Radomski that they couldn't get engaged until Shrinking wrapped because it was "very overwhelming." Then, he lied about why they needed to go to the botanical gardens, making up a fake "donor dinner."

"As time went on, I really couldn't hold this lie very well at all," Segel said. "So I kept adding things like, 'I heard the mayor's gonna be at the donor dinner.' And I said, 'I heard the LA Times is coming to the donor dinner.' By the time this night arrives, it sounds like a total chore."

Upon arrival, the Huntington Gardens staff also played into the act, welcoming the couple to the after-hours "donor dinner." When Radomski saw a carpet covered in rose petals in front of a Greek statue, she assumed it wasn't for her, telling Segel, "Aw, someone must have just gotten married here."

It was time for the big moment.

"I said, 'Yeah, this is the love statue. Close your eyes, make a wish,' " Segel recalled. "And while our eyes were closed, I got down on my knee, and I proposed."

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Initially, the Forgetting Sarah Marshall star thought that he didn't reach his goal of making Radomski "cry real hard" because he saw just a single tear. He thought to himself, "This is not enough crying," but when the string quartet began playing "Tale as Old as Time" from Beauty and the Beast, Radomski's "favorite movie," the floodgates opened.

"She lost it," Segel said.

Kayla Radomski and Jason Segel in March 2026Credit: Amanda Edwards/Getty

The actor proposed with a ring he designed himself.

"Kayla's this amazing mix. She presents as a Disney princess, but she's a total weirdo," Segel said. "And so I wanted something that really captured who she was, and I think I did it."

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Radomski announced their engagement on Instagram on June 18, 2025, by sharing photos from the romantic proposal, which Segel said on Jimmy Kimmel Live! were taken by "a friend hiding in the bushes dressed as a tree." The So You Think You Can Dance alum wrote in the caption, "FOREVER YES 💍♥️."

The couple celebrated their engagement in January with a party at the restaurant Cannonball in South Pasadena, California. In a since-expired Instagram Story video posted by Radomski at the time, Segel could be heard saying, "I can’t wait to get married to Kayla."

"Man, I'm having a really good time," Segel added on Jimmy Kimmel Live! "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."

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Source: “AOL Entertainment”