Kory Keefer’s age compared to Jessica as they hook up on Winter House Fri 11 November 2022 11:57 Updated Tue 3 October 2023 08:01 Celine Byford
Michael Green
Published Apr 06, 2026
Kory Keefer and Jessica Stocker entered Bravo’s Winter House as the series’ newbies for season 2. After they hooked up on the November 10 episode, many are asking what his age is compared to Jessica.
Business owner Kory and real estate agent Jessica are both entrepreneurs running their own projects, but have now launched another: their romance. After a short-lived fling with Luke, Jessica and Kory ended up in bed together.
So, just how old is Kory compared to Jess? Reality Titbit looked at their age difference, and got the latest juicy recap on exactly what’s been going on between the two of them. The last episode showed Jessica in Kory’s bedroom.
Just catching up on #WinterHouse and I’m all for women empowerment and what not but Jess & Kory rn is…. on national tv?? 😬
— EAO (@emma_oyomba) November 11, 2022
Kory Keefer’s age
Kory is 32 years old and celebrates his birthday on August 16. In 2016, the Core 24 Gym founder and thrill seeker took his employees skydiving and described him as “fearless” for spending his birthday in the air.
He joined the line-up as Craig Conover’s best friend, who was his roomie through college. Kory went to the same fraternity, Kappa Sigma, as his Winter House co-star, and the two have since been friends for years.
Kory was born in Maryland and raised in South Carolina, at the College of Charleston. In his early thirties, he owns two businesses: Core 24 Gym in North Carolina, and media and film company Culture V Clout.
HAPPY BIRTHDAY to our fearless leader, Kory Keefer! Always thinking outside the box, he creates an environment that…
Posted by CORE 24 GYM on Friday, August 19, 2016
How old is Jessica Stocker?
Born in 1997, Jessica is 25 years old. At an early age, Jessica realized her passion for sales and relationship building and has since gone on to become a real estate agent who runs Blondes Building Equity with her best friend Kinsey.
From Salem, Oregon, she celebrates her birthday on March 15. She went to McNary High School growing up but now lives in Beverly Hills, California, where she moved to in September 2017.
Jessica is seven years younger than Kory, one of the largest age gaps between two stars who have had romantic encounters on the show. Winter House couple Craig Conover, 33, and Paige DeSorbo, 30, are three years apart.
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Winter House: Kory and Jessica’s hook up
Kory and Jessica were seen being intimate in bed together, before she went back to her own room. However, he has also admitted on Winter House that he is “kind of pursuing all of them [girls in the house].”
Jessica has been calling him “babe” while the two were flirting with each other for a while. However, they have both had romantic bonds with co-stars, including Kory hitting it off with Ciara and Jessica’s romance with Luke Gulbranson.
The night before Jessica and Kory hooked up, he had told her he wouldn’t sleep with her, to which she responded: “You don’t?” However, things changed when she was in his bed the following evening.
At one point, she could not remember his name and accidentally called Kory Craig. He then said, “I literally can’t with you,” before Jessica laughed. He then announced that he is going to bed again.
Kory tells me he is exactly who I think he is in this scene. #winterhouse
— Countess and Frenemies ✨ (@CntessNfrenemy) November 4, 2022
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