Welp, you can say a lot about Craig Conover, including the fact that he is a lawyer and a storyteller, but you officially can’t say his story that he bought an engagement ring for Paige was a lie! After Craig made it clear the breakup wasn’t mutual because, in his mind, he and Paige were mid-planning forever, Paige had a major bone to pick with Craig’s talk of a ring she never saw. In fact, Paige and her entire crew of Summer House castmates laughed at the mere notion of this supposed ring at the Summer House reunion. Now (unless Craig is a master photo fabricator, which, as an elder millennial, I highly doubt), he’s finally come forward with some receipts that the rock in question did exist! Why the pillow princess decided to reveal this on Southern time is beyond me, but nonetheless, here are the details of Craig’s engagement ring for Paige.
Craig’s Ring For Paige: Pictures
Did Craig Conover actually buy an engagement ring for Paige?
It would appear that Craig did, as he said, buy Paige a ring before the breakup! On a June 24, 2025, podcast episode of The Toast podcast, Craig showed the red-headed Oshry sis a picture of the ring, to which she immediately responded, “Oh, wow. Oh, it’s so beautiful!” Craig pointed out that when you zoom out of the picture, you can clearly see the diamond is in a formal ring box on his nightstand in Charleston.
More than that, Jackie Oshry clicked on the iPhone’s geolocation feature and confirmed the picture was taken in Mount Pleasant, Charleston, on March 11, 2024 — long before the breakup and before the reunion. Soooo… unless Craig came up with a foolproof way to hack an iPhone or borrowed a random ring to prepare for this elaborate and very tardy cover-up, the picture and its contents appear to be authentic. Damn! Are Paige, Kyle, Amanda, and co. ever going to apologize for laughing about how impossible it is to return a ring? Probs not!
Craig explained that he and Paige had “a pretty decent life offline,” so he didn’t feel like fans were “entitled” to proof about his rumors he knew weren’t true. He claims that if someone had “just [asked] me to see it,” Craig would’ve shown it. Craig, honey, Andy Cohen, and I have been asking for weeks!
How did Craig return the engagement ring?
“Now returning it, now that’s a weird day,” Craig explained. When Craig bought it, the commercial diamond jeweler told him “in case anything happens,” he’d “work with [Craig],” a policy this jeweler tells everyone purchasing a ring for a proposal, which could go one of two ways. Wow, small-town hospitality goes craaazy! Craig doesn’t get his money back until the ring resells, however.
