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.
Chelsea is jealous when Charlie's ex fiancé, Mia, calls him--perhaps rightfully so. Meanwhile, Judith goes into labor, Herb is incapacitated, and Alan runs into his ex-girlfriend and receptionist at the hospital.