Season 5: Episode 3 - Dum Diddy Dum Diddy Doo

Dum Diddy Dum Diddy Doo: Tired of dating bimbos and being the oldest guy at the bar, Charlie goes on a blind date with a municipal court judge, Linda (guest star Ming Wen). She’s an intelligent, attractive, age appropriate, single mother who is clearly way out of Charlie’s league. Their first date goes horribly, as Charlie can't help but put his foot in his mouth, and the relationship appears to be over before it starts. After several attempts to get in touch with Linda, Charlie gets arrested while out on the town, and has to appear in front of a judge, who just happens to be Linda. Linda thinks Charlie's arrest was just a ploy to get to see her again and Charlie slyly goes along with that notion. She agrees to have dinner with him again as long as he stays out of trouble. At home, Jake wants nothing else but to be on the phone with his girlfriend. Whether he's at the dinner table, watching TV or in the car, he's got the handset glued to his ear. But when picking up Charlie from the jail, Alan finally cracks and throws the phone out the car window.