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!”  Start your 7 Day Free Trial of Viall Files + here: https://viallfiles.supportingcast.fm/  Please make sure to subscribe so you don’t miss an episode and as always send in your relationship questions to asknick@theviallfiles.com to be a part of our Monday episodes. Join us for our new LIVE show on Thursdays at 9PM ET/6PM PT on Amp, available in the Apple app store. Android User? Listen here: https://www.onamp.com/  To Order Nick’s Book Go To: http://www.viallfiles.com  If you would like to get some texting advice on Office Hours send an email to asknick@theviallfiles.com with “Texting Office Hours” in the subject line! To advertise on the show, contact sales@advertisecast.com or visit https://www.advertisecast.com/TheViallFiles  THANK YOU TO OUR SPONSORS: Alo Moves -  For a limited time, Alo Moves is offering our listeners a free 30-day trial PLUS – get this - 50% off an annual membership. But you can only get it by going to https://www.alomoves.com and use code NICKVIALL in all caps.  BetterHelp - Discover your potential with BetterHelp. Visit https://www.BetterHelp.com/VIALL today to get 10% off your first month. Episode Socials: @viallfiles @nickviall @barbaracorcoran @nnataliejjoy @alison.vandam @liffordthebigreddog @dereklanerussell