Welcome back to The Viall Files: Going Deeper Edition! Today we are joined by Barbara Corcoran to talk business, love, and pop culture. What were the defining moments of her career, what does she think about modern dating and hook-up culture, and how about flirting with Nick? We then have a "Sweating the Wedding" bridesmaid who has been plagued by Venmo requests from a very bougie Maid of Honor… the bachelorette trip is quickly approaching, and she's worried about the potential budget and charges coming her way.

"Pettiness, me? Of course!"

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