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Kelsea Ballerini’s Awkward Almost-Date with Craig Conover: A Haunting Story!

Kelsea Ballerini’s Awkward Almost-Date with Craig Conover: A Haunting Story!
  • PublishedFebruary 19, 2025

Kelsea Ballerini, the 31-year-old country sensation, is still feeling the aftershocks of a near-miss romantic encounter with Craig Conover from Bravo’s “Southern Charm.” In a recent clip for Cosmopolitan’s “Cheap Shots” game show, she dropped some hilarious and haunting insights about that fateful night nearly a decade ago. During her radio tour, Kelsea thought she was just there to perform her hit “Love Me Like You Mean It” on a boat, totally unaware that cameras were rolling. “Oh God,” she quipped, squirming in her seat when the fan question popped up about the infamous bid for a date with Conover on the show. It seems her label thought it was a grand idea to sneak her into the episode, a decision that left the singer feeling a bit blindsided.

In the episode, the auctioneer pushes up the bidding for Conover, but Kelsea’s dreams of an epic date didn’t materialize. “It was auctioned off for charity,” she explained, revealing that their almost-date went to a random winner from the radio station instead of blossoming into a romance. Despite the ghost of what could have been, she maintains that “everything is great as it turns out,” having moved on to a romance with “Outer Banks” hunk Chase Stokes, who she slid into the DMs of back in January 2023.

As for Conover, he’s had a bit of a rough patch himself, recently splitting from fellow Bravo star Paige DeSorbo. The breakup, which occurred last November, seems to have him re-evaluating his dating tactics. During a Galentine’s Day appearance in Atlantic City, he confessed, “I don’t think a dating app is for me,” lamenting that he’d prefer to meet someone “out in a bar or in life.” With a ring that he had already snagged for Paige, his approach to love seems to be shifting. Could Kelsea and Craig’s almost-date have been just the quirkiest twist of fate? Only time will tell who gets the last laugh in this real-life love saga!

Sources: Celebrity Storm Wire and People Magazine, E! Online, Us Weekly

Written By
Elena West

Elena West is a seasoned journalist with a passion for uncovering the real stories behind the glitz and glamour of the celebrity world. Known for her meticulous research and sharp writing, Elena brings a thoughtful and compelling voice to every piece she tackles. With an eye for detail and an ear to the ground, she’s able to break through the noise and get to the heart of the story. When she’s not tracking down the latest scoop, Elena enjoys exploring new cultures, binge-watching true crime documentaries, and curating the perfect playlist for every mood.