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Brynn Whitfield Dishes on Her Flirty Encounter with Captain Jason Chambers!

Since meeting Brynn Whitfield, we’ve learned that she isn’t afraid to share candid confessions. And, it’s clear that nothing has changed for this big city girl.

The Real Housewives of New York City cast member made a surprise appearance on Watch What Happens Live with Andy Cohen on Sunday, Aug. 11, where she dished on the upcoming RHONY season and talked about who she hit it off with back at BravoCon 2023.

Yes, this includes Below Deck Down Under‘s Captain Jason Chambers (who definitely caused a stir that weekend with several Bravolebs).”Were there any cute guys you connected with?” host Andy Cohen asked Brynn during her recent Clubhouse appearance.

“The guy from the boat show,” she replied, with Andy noting it was Captain Jason. “Yeah, he’s cute. And you know I love yachts.”

As you might recall, at BravoCon 2023, Captain Jason did note that Andy seemed to want to play matchmaker for him while they were in Las Vegas. “I’ve been trying to set you up with every woman at Bravo. How’s that going?” Andy told the Captain last November.



Captain Jason shared: “I don’t think anyone else could try any harder than you have [to set me up]. It’s a slow burn.”

Brynn Whitfield opens up about hanging out with Shep Rose

But, as Andy pointed out, Brynn didn’t end up making a connection with Southern Charm’s Shep Rose. “That’s your fault. That is all your fault; I blame you,” Brynn told Andy.

Brynn Whitfield wearing a red dress at Watch What Happens Live in New York City.

Photo: Bravo

“It’s not my fault, actually,” he replied.

Andy had tried to set up Brynn with Shep at the Las Vegas convention held in November of last year after both of them expressed their interest in one another. But, things didn’t work out between them. Brynn and Shep got a drink together that same weekend, but ultimately, Brynn pushed him in the friend zone.



During a May appearance on Bravo’s Hot Mic podcast, Brynn revealed that she was “not feeling it” between them. “He very much reminds me of someone I dated in my early 20’s,” she said.

What Is Brynn Whitfield Doing in RHONY Season 15?

Brynn might not be hitting it off with Shep any time soon, but she will be causing a stir on RHONY Season 15 which premieres this October. Brynn will be focusing on her future in this new season, and it sounds like it won’t always be too easy for her.

Per her cast bio, “Life for Brynn Whitfield is as sweet as can be since moving into her dream apartment with her energetic puppy, Sugar. Now that she’s perfected her new space and settled into life as a dog-mom, she’s ready to explore the next chapter: motherhood. But as rumors begin to swirl, she finds the life she’s worked so hard to create is questioned.”