Charlie kicks Alan out of the house again after Alan demands that Charlie pay him back the $38 he owes him. Alan and Jake are now forced to turn to Judith and Herb for a temporary home.
Charlie gets more than he bargained for when he tries to make amends to one of Jake's old teachers that he dated, who went off the deep end and became a stripper after he broke up with her.
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.
Charlie's month-long relationship threatens to go down the tubes when she asks him to spend the night at her house instead. Alan grounds Jake for mooning some girls on a school bus.
Judith is pregnant, Alan believes he is the father, and Judith tries to keep him away from Herb. Meanwhile, Charlie tries to figure out why Jake is so irritable.
After his family acts mean-spirited during Alan's "surprise" birthday party, Alan decides he's had enough and moves in with his girlfriend and her mom.
Charlie needs Alan and Jake's help getting rid of the drunk, half-naked bimbo passed out in his bed when his girlfriend tells him she's coming home early from a funeral.
Charlie is so desperate to get Chelsea to return his accidental "I love you" and not lose control in the relationship that he is willing to propose to her just to make her say it.
Chelsea is jealous when Charlie's ex fiancée, 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.
