'Dum Diddy Dum Diddy Doo' - Season 5, Episode 3
Alan convinces Charlie that he needs to date more respectable women and sets him up with a judge. The two double date and their waitress happens to be one of Charlie's ex-girlfriends. Desperate for a second chance, Charlie goes to great lengths to speak to her again.
Air Date: October 7th 2007.
Charlie: Yeah, hi, Linda, it's Charlie again. I just want you to know this will be my last message. I figured three's a charm, four is a restraining order. (Laughs) Look who I'm telling.
Alan: Oh, there they are.
Charlie: Hang on, hang on, which one's mine?
Alan: The one on the right.
Charlie: Wow! She's forty? She has the ears of a twenty-year-old.
Linda: Old friend?
Charlie: Oh, yeah! You know, church choir, bake sale. You may not want to drink the ice tea.
Alan: Oh, hey, how was Santa Barbara?
Jake: Santa Barbra? It's Spanish for "city of great racks."
Charlie: Rose? Nah, couldn't be. I'm so backed up I'm literally cock-eyed.
Charlie: 40 year old women have alot of baggage.
Alan: And you have a carry-on.