Bert Kreischer tells his notorious ‘Machine Story’. Topher Grace shares what it was like working with Anna, some pointed advice that he gave her., and going out on the town with Wilmer Valderrama. David Spade learns that Unqualified is a relationship podcast while playing Deal-Breakers. Kat Dennings plays Swipe Left or Right. Bobby Lee gets ‘interviewed’ by Gwen Mandy on the morning show, Iced Latte Today. Sophia Bush discusses being single and shares her thoughts on self-love and dating. Macaulay Culkin talks about losing his virginity. Adam Rippon gives Anna the low-down on hooking-up at the Olympic Village. Jay Pharoah meets Karen Sarducci and impersonates Eddie Murphy. Bella Thorne and her sister, Dani, join Anna to help a caller struggling with trust issues in her relationship. Pete Holmes and Anna offer brilliant advice to a caller that’s having trouble with her boyfriend’s friends.