Charlie is acting even more promiscuous than normal, which is getting him in trouble with a lot of husbands and boyfriends. With the help of his psychiatrist, he discovers it's related to his ex-fiancée's upcoming wedding.
Charlie dates a self-help author who is much older than him, has a 32-year-old son, and treats him more like his son than his boyfriend. Jake tries to write a book report over the weekend, but keeps losing the book before he can read it.
Alan is overjoyed when he learns that Judith and Herb's marriage is on the rocks, but he gets more than he bargained for when he tries to fake-comfort her. Meanwhile, Herb tries picking up women with Charlie's help.
Alan and Judith start seeing each other again after Judith's breakup with Herb, Herb continues to turn to Charlie for help picking up women, and Charlie messes with Jake by threatening to get him sent to military school.