Conover, who has been part of the reality series since its 2014 start, connected with Kroll in 2016 when he started filming with the Charleston, South Carolina, residents. Unlike most of the original cast who come from Southern aristocracy, both Conover and Kroll are working men.
Their struggles to get their careers off the ground — Conover is the founder of Sewing Down South while Kroll is the suds master for Kings Calling Brewing Co. — is only part of what brought them together.
After breaking off their respective romances — Conover split from Naomie Olindo in 2017 and Kroll and Madison LeCroy called it quits for good in December 2020 — the pals embraced life without girlfriends.
The attorney and the North Carolina native’s single status caused a bit of controversy in December 2020 after the pair sparked up a friendship with Kristin Cavallari a few months prior. Following a trip to Nashville, some fans thought Kroll was more than just friends with the True Comfort author.
Conover exclusively told Us Weekly at the time that his longtime friend needed to “heal from his trauma” with LeCroy before he would seriously consider dating Cavallari, who split from husband Jay Cutler in April 2020 after nearly seven years of marriage.
The Delaware native said he would be “fine” with his Southern Charm costar dating Cavallari in the future, noting that fans hadn’t seen the last of their new friendship group, which also included Cavallari’s BFF Justin Anderson.
“I think you saw our chemistry the other night and when Taylor Swift comes on, all of the walls come down and apparently we go live,” Conover told Us. “We’ll have to see what happens. I don’t know. I can’t speak for them, but I think you’ll see a lot of the four of us in the future.”
Seven months later, Conover was romantically linked to the Very Cavallari alum himself when rumors surfaced that the Balancing in Heels author was in a love triangle with the two Bravo reality stars.
Cavallari denied the allegations in July 2021, but the relationship rumors made headlines again in January 2022 after Conover claimed during a Summer House episode that he had “hooked up with her before.”
During the episode, which filmed in July 2021, Conover claimed that Kroll was jealous of the romance. However, a source exclusively told Us at the time that Cavallari “never hooked up” with the southern gentleman.
Despite their rumored love triangle with Cavallari — and butting heads on Southern Charm on more than one occasion — Conover and Kroll can’t help but gush over each other.
“There’s a really fun side to his personality. We travel together a lot,” the Charleston School of Law graduate said during an October 2021 appearance on Watch What Happens Live With Andy Cohen about Kroll. “There is a side to Austen that’s very lighthearted and fun and funny and fun to be around.”
Scroll down to see Conover and Kroll’s friendship ups and downs: