Connie and Kate bond at a local bar when the conversation drifts to Kate's challenges of being wealthy. Later, just at the peak of tension between families, Roman tells of the time at his and Kate's wedding when he overheard a conversation between Chet and their father-in-law describing how they think Roman is a crooked businessman. This leads to Roman telling Chet why he came up to visit: To offer Chet a $25,000 investment opportunity. Chet, feeling guilty from the wedding story, is at first reluctant, but eventually agrees to write Roman a check for the whole amount. The families say their goodbyes and Roman and his family head back to Chicago. On the car ride home, Kate praises Roman for including Chet in the investment, noting that $25,000 is a lot of money for them. Roman, now feeling his own sense of guilt, suddenly stops the car and turns back to the cabin.