Bored to Death: The Alanon Case

During an unsuccessful attempt to win back Suzanne, Jonathan gets a phone call and a new case: a woman named Jennifer (Kristen Wiig) wants him to tail her boyfriend Gary (Peter Hermann) to see if he's been unfaithful. After learning that he and Jennifer share a common pastime (drinking), Jonathan heads out in search of her boyfriend—with uncomfortable results. Meanwhile, Ray brings Jonathan along to his colonic for moral support, and George hatches a knockout plan in which Jonathan will help him cover up an unsightly sore before a big speech.