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Features

Craig Conover’s Dating History: Naomie Olindo, Paige Desorbo, Kristin Cavallari, and More

March 31, 2025

By Amy DeVore

Craig Conover Southern Charm — Photo Credit: Paul Cheney/Bravo/NBCUniversal via Getty Images

Craig Conover and Paige Desorbo are no more. Before Paige, Craig dated other starlets, like Naomie Olindo and Kristin Cavallari. Okay Craig did not date Kristin, but they did have a fling of sorts whilst Craig was between partners.

Paige and Craig lived in different chapters in separate books. Craig was ready to propose to Paige,…

Amy is a former teacher who used reality television as a form of escapism during her decade spent in the classroom. In addition to education, she also studied and performed long-form improvisation while mastering the art of comedic sketch writing via the Upright Citizens Brigade Theater in NYC. Amy has interviewed reality television stars from the Real Housewives and Below Deck franchises, as well as each of the winners from E!'s OMG Fashun.