The last time we saw Paige DeSorbo and Craig Conover on TV, they were two little ski bunnies in Vermont. The stars were nothing more than friends on Winter House, mostly because Paige was falling in love (almost instantaneously) with Andrea, the Italian model who descended upon the slopes out of nowhere. (Just kidding, he came from Paige's dreams.)
However, Paige and Andrea's relationship is no further along at the premiere of Summer House this season than it was in Stowe, and we know that Paige and Craig are dating now... so I guess, if I were a meme, I'd be the confused math lady, because how did these two get together and when was Andrea given the fine Italian leather boot?
February 2021: Winter House films
The pair definitely were friendly on the show, but both were otherwise engaged (Craig to his girlfriend at the time Natalie, Paige to Andrea's abs and accent.)
April 2021: Paige and Craig are seen together in Charleston
Despite being spotted together in Charleston, Paige still denied that they were together. On the Not Skinny But Not Fat Podcast, Paige explained that, "Craig and I are a thousand percent not dating... Craig and I have known each other for years. We’ve always gotten along. We’ve always been friends. We have, like, very similar personalities. We are not romantically involved or anything, but we are very good friends.” Paige has since confirmed to Entertainment Tonight that Craig kissed her on the end of that trip.
May 2021: Paige flies to see Craig
While the exact date that Natalie and Craig broke up is still unclear, Craig did say on the May 1 episode of his podcast, that he was "going through, like [a] break up." Paige revealed to Entertainment Tonight that she actually flew down to visit Craig in May as well. She says, "he asked me to come down and spend a weekend with him and that is what really started us hanging out, but we were very single... we loved the time that we were together and hanging out. So we were very much casually dating."
July 2021: Summer House starts filming
Paige says in the first episode of Summer House Season 6 that she had been casually seeing Craig, but was clearly torn between him and Andrea.
Summer 2021: Summer House filming continues
We will definitely see their relationship progress on this season of Summer House. Paige even tells Entertainment Tonight that the clips we see of their date in the Bravo "First Look" was actually their first date. So, we can assume if this is when they considered themselves "dating," as in going on dates, Andrea may officially be old news.
Craig and his bestie, Austen Kroll, are featured multiple times in the trailer, too, so we know they were there at some point during the summer, if not multiple times.
August 2021: PGA Tour
The pair were spotted together at the PGA tour in Jersey City.
September 2021: Kymanda's Wedding
Personally, I'd consider this the moment they became official, even if they didn't confirm it. Instagram (story) official isn't a thing for no reason!
October 2021: Halloween
Paige Six broke the news that they are "officially together." The pair spent Halloween together as well.
November 2021: Thanksgiving
Paige told E!'s Daily Pop that the pair spent Thanksgiving with both sets of their parents. Official couple things.
December 2021: Winter Gala
The pair were together at a winter gala together down in Charleston. This is actually the first post on the Instagram feed... so another big step in their relationship.
Image: Instagram, @paige_desorbo