Laura, a humor-free executive, seeks Amy's guidance on being funny in the workplace; Amy has to go under cover as a man to prove women are funny; a chipmunk eats a snake.

Amy flies to Miami to help Livi, a college student struggling with the city's sexiness; together, they experience all that Miami has to offer including dancing, food, double decker buses, and a hurricane.

Amy cares for Gilbert, a recent college graduate who suffers massive anxiety over getting his first job; Amy's own anxiety drives her to Loch Ness where she discovers a monster might just be part of Gilbert's solution.

When a married couple consider polyamory, Amy opens her mind to help open their relationship; Amy learns the ins and outs of non-monogamy and goes undercover to find out whether more is truly the merrier or three's a crowd.

Rocker Collette asks Amy for help reconciling with her old friend and drummer, Tom; Amy goes to the ends of the Earth to dig up unlikely experts and does whatever it takes to get these former friends in the same room.

Nine-year-old Matthew is tired of his father's nonstop teasing; Amy seeks help from a Marine sniper to plan a sneak attack at a family barbecue to give Matthew a taste of payback, but he learns that revenge is a dish best served not at all.