After Judith asks Alan to take care Jake for three straight months, Alan and Charlie discover it's because she and Herb are having marital problems. Later, Herb comes over to drop some things off for Jake and Charlie offers him some bad advice on how to deal with Judith. Herb does as Charlie suggests and Judith kicks him out. He then tries to get Charlie to hang out with him, and after Charlie repeatedly ignores his calls, he tracks him down at Pavlov's. Meanwhile, Alan is thrilled by the problems Herb and Judith are going through, as they prove he wasn't the only one to blame in the destruction of their marriage. He goes over to Judith's to gloat about it but ends up sleeping with her as she informs him that she is never, ever going to let him go, freaking him out about what's to come.