Single Guy David from Enumclaw has written to Fitz saying he is ready to meet someone new. We have offered him a choice between City Girl Becca from the Seattle neighborhood of Ravenna and Country Girl Kristi from Marysville. Becca has tickets to some kind of crazy 1920's party on a boat so she proposes a day of thrifting for crazy clothes, enjoying the boat ride with food and jazz, and then going to 13 Coins for some all-night people watching. But Kristi suggests that's too much stuff and what David really needs is a nice, chill Country night of downhome food and drinks at Loco Billy's followed by a little star-gazing. David has said he wants to do something more than his "regular old Country lifestyle" but Country Girl Kristi does give a good pitch, as does City Girl Becca. So who will David pick? And will they actually go through with the date?