Season synopsis
Contains spoilers for this season and earlier seasons.
Season four opens with Alan married to Kandi and living away from Charlie. In Las Vegas, the newlyweds win $500,000 on a slot machine, but the episode jumps four months: their marriage has collapsed, Kandi has divorced Alan, and he returns to Charlie's house broke and devastated. Judith has moved on with Herb, while Alan resumes sharing a home with Charlie and trying to stay involved in Jake's life. Kandi's departure does not end her story immediately: later she auditions for a forensic-investigation series called Stiffs, reconnects with Alan, and they revisit the disagreement that ended their marriage—she wanted a baby and he did not.
Alan tells Kandi he has changed his mind about having a baby, and they decide to try again. When the call comes confirming she got the Stiffs role, Kandi signs their divorce papers and accepts the job, ending their brief reconciliation. Charlie, meanwhile, reacts to Rose's announcement that she is moving to London and begins seeing Myra, Herb's sister, around Judith and Herb's wedding. The finale introduces Evelyn's new boyfriend, Teddy, who takes Charlie, Alan and Jake to Las Vegas on his private jet. The brothers initially struggle with their mother's latest partner, remembering how often men came and went during their childhood, but Teddy treats them generously and wins them over. They end the trip deciding they like him, giving Evelyn's new relationship a warmer family welcome than her sons usually offer.