D.L. opens up about the personal cost of political divisions, revealing how he's lost relationships and even fired an agent over Trump support. The conversation turns to the awkward reality of friendships strained by politics and the questions we all hate being asked - from "Why are you still single?" to "When are you going back to church?" The crew discovers that AOL dial-up internet is finally shutting down, leading to hilarious confessions about ancient email addresses and digital archaeology. D.L. promotes his upcoming City Winery show with Don Lemon while sharing funny stories about Don's pistol of a mother from New Orleans who helped bring the two hosts together.