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Jack and his staff try to land a new client with a group of monks who train dogs. Meanwhile, Jack tries to deny that he's on the rebound and aggressively pursues a therapist, Carrie Dover. However, the monks' secretary Susan, goes after Jack when she finds out he single and forces him to a date. Alex tries to set her dad up with her boss Grace, and Alex's strange co-worker Julie also goes after Jack. When Jack and the others are showing the campaign to the monks, all the women show up and all get angry. Jack tries to convince Carrie to still go out with him but she only agrees to be his therapist since he is obviously confused.