Kory Keefer, a longtime friend of Craig Conover's, is joining Winter House season 2 on Bravo to stir up some drama. Winter House season 1, a spin-off of Summer House, aired in October 2021. The show follows several cast members from Summer House and Southern Charm alongside other friends as they travel to Stowe, Vermont for a two-week winter getaway. Relationships were developed over the course of the trip, and drama unfolded as cast members dealt with intense emotions in such close quarters. With Winter House season 2 on its way, the cast has several new cast members like Kory, such as Rachel Clark and Jessica Stocker, who will undoubtedly bring new and exciting dynamics to Winter House.

Winter House season 1 provided viewers with a season full of ups and downs, and the second seems to be doing the same. The Winter House trailer teased drama between many cast members, including Summer House's Amanda Batula and her husband Kyle Cooke, as well as Southern Charm's Craig and his Summer House girlfriend, Paige DeSorbo. It seems as though Kory, who comes to the house a single man, might be juggling a few different relationships throughout the season. As other housemates know, Winter House romances can easily sizzle or fizzle when under the same roof. Whether Kory will successfully navigate through the relationship drama of the house remains to be seen.

Related: Why Winter House Is The Show Bravo Fans Deserve

Kory, who was born in Maryland and raised in South Carolina, met Craig while they were in college. According BravoTV to Craig and Kory were members of the same fraternity, Kappa Sigma, at the College of Charleston. In his book, Pillow Talk, Craig says he and Kory were “inseparable” and had “developed a bit of a reputation as the same guy, just in different bodies” until they experienced a fallout. When Craig was cast on Southern Charm, he had initially thought Kory would be on alongside him. Kory had met with producers and cast members along with Craig, who is a good match for Paige, but ultimately he did not make the cut. Kory went on to travel and opened a gym in South Carolina, reconnecting with Craig before joining the cast of Winter House this past year.

Winter House season 2 cast

In his cast bio, Kory is described as an “adrenaline junkie” who quickly becomes the “house heartthrob” in the house. The recently released Winter House season 2 trailer shows Kory, who says he is “pursuing all” of the single women there, seemingly flirting with fellow newcomers Jessica and Rachel, as well as Winter House alum Ciara Miller. This will surely stir up some emotion for Austen Kroll, who spent the last trip to Vermont romancing Ciara, who would hook up on and off for less than a year.

For new cast members like Kory, it can be a bit overwhelming to join an already formed cast. Thankfully for Kory, with his existing connection to Craig, who might have Paige join Southern Charm, it seems he should easily get along with the other cast members. While the Winter House trailer portrays him as a bit of a player, it's unclear whether Kory will ultimately settle on one woman to pursue in the house or continue to play the field. While Kory does not seem to have a social media presence, he may join in once Winter House season 2 premieres on October 13. With Kory's storyline surrounding multiple relationships, he may have some explaining to do.

Source: BravoTV