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The Daily Dish Winter House

Kory Keefer Shares a Surprising Tidbit About Craig Conover and Paige DeSorbo’s Relationship

The Winter House-mate had an interesting take on when Paige and Craig will get engaged. 

By Shannon Raphael

As one of Craig Conover's longest-standing friends, Kory Keefer has a unique perspective on the Southern Charm-er's relationship with Paige DeSorbo.

How to Watch

Watch Winter House on Peacock and the Bravo app.

The pillow magnate has been in a long-distance relationship with the Summer House castmate since the fall of 2021, and the two have talked at length about moving to the same city and taking the next step in their relationship. 

After hearing Craig previously say that he was going to propose to Paige by Thanksgiving 2023, Kory revealed when exactly he thinks that his former fraternity brother will be popping the question. 

Kory Keefer Shares a Major Update on Craig Conover's Relationship with Paige DeSorbo

In case you need a refresher, while Winter House Season 2 was airing in November 2022, Craig and Kory appeared together on an episode of Watch What Happens Live with Andy Cohen.

When asked on the show about a potential engagement timeline for him and Paige, Craig said that he would be engaged within a year. 

“Hopefully it’ll be before Thanksgiving," Craig said about his 2023 goals, though that obviously did not happen. 

Fast-forward to when Kory appeared on the December 12 episode of WWHL, and he offered host Andy Cohen an update on Craig's plans. 

"Last time I was with Andy on Watch What Happens Live, [Craig] said he was going to do it in a year, and it's pretty much at that mark, so, and it hasn't happened," Kory said on the late-night series, which you can check out by watching the video at the top of this post. 

However, Kory does believe that an engagement is imminent. 

"Yes, 100 percent it's gonna happen," the Winter House castmate added. "Within a year, he's gonna be popping the question, for sure."

composite of Kory Keefer at Bravocon 2023 and Craig Conover with Paige Desorbo at the Variety Women of Reality event

Kory Keefer Says Something Surprising About Paige DeSorbo's Engagement Vision

The gym owner went on to offer some insight into Craig's possible proposal plans. 

"Paige says she doesn't want it to happen on the show," Kory continued about the Summer House-mate, who has also appeared on Southern Charm and Winter House. "She was like, 'I don't want that to happen,' so it might be behind the scenes and then they show it afterwards."

As Bravo fans eagerly await news on a potential engagement between the Southern Charm-er and the New York-based Summer House cast member, they can catch up with Craig and Paige by streaming both shows on Peacock. 

The Winter House Season 3 finale airs on December 19, and the reunion will air as an episode of Watch What Happens Live with Andy Cohen on the same day.

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