Craig Conover Shares When He’ll Propose to Paige DeSorbo

Craig Conover has set yet another deadline for himself.

After failing to propose to girlfriend Paige DeSorbo, 31, by Thanksgiving of last year, as he announced he would do during a past episode of Watch What Happens Live, the Southern Charm cast member, 34, returned to Andy Cohen‘s late-night talk show with another timeline as he also spoke of Shep Rose‘s drinking habits, his kinkiness, and if he’s heard from Shep or Taylor Ann Green, 29, in regard to Paige’s issues with them.

After being asked when he’ll propose to Paige on the January 18 episode of WWHL, Craig said, “September will be three years. I think between two and three years is an appropriate time to get engaged.”

Then, after confirming he would propose to Paige before September, stating, “We’re gonna go with that,” Craig admitted he shouldn’t be trusted when it comes to setting timelines.

“They don’t mean anything,” Craig laughed after Andy mentioned his past deadline of November 2023.

When a caller then questioned Craig about why there is so much pressure on the Summer House star to move to Charleston when he can move to New York City, Craig said he agreed that the pressure Paige is under isn’t fair.

“I think there’s a lot of outside pressure put on and I agree with that statement. I have no idea what we’re gonna do but I think it should be equal pressure,” he reasoned.

Following Shep’s admission of having a drinking problem at the Southern Charm reunion, both Craig and fellow guest Austen Kroll, 36, offered an update on WWHL.

“He did something very Shep that he’s excited to tell everyone about … He said it changed his life. He went to a retreat in Costa Rica and he’s sticking to drinking beer. I’m excited to see what the next chapter is,” Craig revealed.

As for Austen, he added, “I’ve spoken with Shep and he’s making active strives to temper his drinking and he just took a trip to Costa Rica … [But] I’m not gonna say what he did there.”

Later, on the WWHL: After Show, Andy, 55, asked Craig about his kinkiness.

“It’s really fun to find someone that you can be like, live out your life fantasies with, and I think it brings connection,” Craig replied. “Sexting is the gateway to that. If you can sext each other videos you like or messages you like, it’s a non-shy way to do it.”

According to Craig, he and Paige actually use a relationship app, called Paired, to amp up their bedroom activities.

“They’ll put up a certain thing, like kink, and you hit yes, no, maybe, and then it matches them together with your partner,” he revealed. “Everyone should have a kinky side, it’s just not everyone has met the person that allows them to be their true self.”

Craig then shared if he’s heard from Shep or Taylor since Paige said she didn’t like them.

“Taylor kind of proactively took some jabs at [Paige], and we were cool with her until she came on WWHL and doubled down on it. Taylor, I was with her a lot during the reunion behind the stage, trying to help her a little bit, but I don’t see a future for her and Paige,” Craig explained. “Shep, yeah I have [heard from him], because Shep knows that he’s burnt a lot of the bridges in his life, and I think he’s trying to repair them which is good.”

“I can’t speak for Paige, but I am open to repairing bridges with both of [them],” Craig added.

Southern Charm is currently on hiatus.