Montana Jordan Got Emily's Help In Real-Life Proposal, Years After Their Initial Awkwardness On Set

Emily Osment recently disclosed that she asked for an intimacy coordinator due to an uncomfortable age gap with Montana Jordan. Did you know that she helped him with his real-life proposal?

Priyanka Dutta

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Montana Jordan Got Emily's Help In Real-Life Proposal, Years After Their Initial Awkwardness On Set

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Ever since Jessica Radloff's book Young Sheldon: The (Juicier-Than-Meemaw’s-Brisket) Inside Story of the Hit Comedy hit the shelves on October 20, 2026, several new pieces of information have left the fans of the show in awe. CBS series Young Sheldon premiered in 2017 and ran for 7 seasons, ending in 2024. 

Now, Jessica Radloff, author of the 2022 bestseller The Big Bang Theory: The Definitive, Inside Story of the Epic Hit Series, released a follow-up that shares several oral histories and behind-the-scenes anecdotes from Young Sheldon. 

Among others, Emily Osment's revelation grabbed attention when she said she wanted an intimacy coordinator on set because she had to shoot with a co-star 12 years younger, Montana Jordan. When they were shooting Young Sheldon, Osment, who joined the series in the fifth season, was 30 years old, and Jordan was 18 years old. 

Emily Osment helped Montana Jordan to propose to his wife in real life

While in reel-life Jordan is married to Emily Osment, Montana Jordan is married to Jenna Weeks in real life, and they are parents to one daughter, whom they welcomed in 2024. Did you know that Montana proposed to Jenna Weeks with the help of his on-screen wife, who is 12 years older than him? Yes! Apparently, Emily Osment was the one to help Montana Jordan (well, we can say partially) pick out the best rock to put in his lady love's hand. 

For the unversed, Weeks and Jordan have been together since 2021, the same year when they met and made their relationship official. The couple got engaged in January 2025 and got married five months later in May 2025. 

Emily Osment helped Jordan by giving her the jeweler's number who made the actress's engagement ring. Emily got married to Jack Anthony in October 2024; however, they ended things shortly after, with the actress filing for divorce in March 2025 and the divorce finalized in September 2025. Returning to how Emily helped Jordan, the actor told Us Weekly that the woman who made Emily's ring was also assigned to make Jenna Weeks' ring after he reached out to her. He said:

"The woman that made Emily's ring, I reached out to her. [Emily] gave me her number and I reached out to her, and that's who created my fiancée's ring. So Emily has helped us through the process a little bit." 

Why did Emily Osment ask for an intimacy coordinator while shooting with Montana Jordan?

At first, things were awkward between Montana Jordan and Emily Osment on set of Young Sheldon, having to make out for the shoot even though they didn't know each other. This has been shared by the director, Alex Reid, too. He revealed that he had a photo of the co-stars from between the sets, where they were seen looking in totally opposite directions. When he showed the photo to Osment, she confessed to feeling uncomfortable.

According to the director, it was not due to the lack of any intimacy coordinator, but it was because of the fact that they had to make out even before getting to know each other. The director said:

"I showed it to Emily and she said, ‘Yeah, that was so uncomfortable for both of us, because we didn’t know each other.' It wasn’t even about the lack of an intimacy coordinator. It’s just you’re having to make out with somebody you just kind of met. Obviously they worked that out, and they have a great chemistry now, but that was kind of embarrassing.”

In Jessica Redolff's book, Emily shared that she felt uncomfortable with the massive age gap between her and Jordan. Osment called Jordan 'a baby with a mullet' and recalled asking for an intimacy coordinator. While initially it couldn't be arranged, the request was granted later, which helped both of the actors, especially because their relationship started to escalate eventually on-screen. 

What do you think about Emily Osment and Montana Jordan's on-screen and off-screen bond?

Photo Courtesy: CBS, Instagram

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