Craig Conover and Kory Keefer’s Friendship Timeline: From Frat Bros to Winter House Roommates (PHOTOS)

Craig Conover’s friendships with Shep Rose and Austen Kroll have been well documented on Southern Charm over the years, but the Delaware native actually has the deepest history with Winter House cast member Kory Keefer.

The pair met while attending the College of Charleston (which is also where the Sewing Down South founder met his now-ex Naomie Olindo), and it was there that they joined the same fraternity, Kappa Sigma. They became fast friends, and later, Winter House castmates.

Both Craig and Kory popped up on Summer House Season 7 just in time for Kyle Cooke’s 40th birthday party, and it’s clear that love is now on the brain for both longtime pals.

While Craig is looking to take his relationship with Paige DeSorbo to the next level — or at least get residency in the same city as her — Kory can be seen making out with newbie Samantha “Sam” Feher in the midseason trailer (she confirmed their relationship to Page Six in April 2023). Find out more about the timeline of Craig and Kory’s friendship by scrolling below.

Craig Conover and Kory Keefer were best friends in college.

On the November 17 episode of Watch What Happens Live with Andy Cohen, Craig and Kory opened up about how they first became friends.

“He was my little brother in the fraternity, and then we lived together for like four years after that,” Craig explained about his connection to Kory. After graduating, Kory and Craig remained tight, but they did hit a major bump in their friendship.

They lost touch when Craig joined the cast of Southern Charm

Kory and Craig had an instant bond when they were in college, but they took a pause in their friendship when the latter College of Charleston alum was cast on the first season of Southern Charm, which debuted in 2014.

Both Craig and Kory were initially part of the Season 1 cast lineup, but Kory said he was later “kicked to the curb.” As a result, the best friends didn’t speak for three years, and Kory ended up spending a year traveling around Europe. They reconciled when Craig asked Kory to come with him on another trip.

“It was my first appearance at, like, a [clothing] store in Florida, and I was able to bring a ‘manager,’ and I called [Kory] and was like, ‘Hey, do you want to go on this trip with me?’” Craig recalled on WWHL. “We met up at the airport and acted like nothing ever happened.”

Fast-forward to 2022, and Kory joined Craig in Vermont for Winter House Season 2. Though Kory romanced Jessica Stocker during the ski trip, he ended up bonding with someone else when he paid a visit to the Hamptons for Summer House Season 7.

Craig and Kory are both appearing on Summer House Season 7

The Southerners reunited with fellow Winter House cast members Kyle, Paige, Ciara Miller, and Amanda Batula on the April 3 episode of Summer House.

Though Kory and Craig were visiting the Hamptons to celebrate Kyle’s milestone birthday, the latter cast member also got to spend time with his girlfriend, Paige, while Kory got to meet his now-girlfriend, Sam. 

Kory, Craig, and their girlfriends now go on double dates together

Though Kory and Sam could be seen kissing in the Season 7 trailer, the latter Bravolebrity only confirmed their relationship to Page Six on April 4. 

“Kory’s my boyfriend! That is so weird. I haven’t had a boyfriend in so long,” she told the outlet about her relationship with the North Carolina resident. “Kory and I made it official a little while ago, and [we’ve] just been enjoying being in a relationship.”

Since Kory and Craig have a storied friendship, and their respective girlfriends, Sam and Paige, connected in the Hamptons, the four often find themselves hanging out together for double dates.

“It’s just really fun for the four of us to be around each other,” Sam said about spending time with her beau, Paige, and Craig. “Like, we’re all kind of obsessed with each other, so it’s a good time.”

Watch Summer House on Bravo Mondays at 9/8c and the next day on Peacock. Catch up on the Bravo app.

Watch Southern Charm on Peacock and the Bravo app.

Watch Winter House on Peacock and the Bravo app.