Charlie struggles with his attitude towards women after his relationship with a woman sours when he can't return her declaration of love towards him and Alan accuses him of being a misogynist. Jake gets contradictory coaching on how to handle a girl who likes him at school from Charlie and Alan.
Tropes
- Oedipus Complex: Rose theorizes that Charlie's inability to be truly intimate with a woman stems from his relationship with his mother and how he saw her treat her husbands.
- Puppy Love: Jake and a classmate named Robin enter a short-term relationship. She gives him a cupcake every day at lunch, and in return, he doesn't talk to other girls, and calls her every night at 6:30. She breaks up with him before the end of the episode.
- The "I Love You" Stigma: Colleen tells Charlie she loves him after a weekend together in bed, and Charlie can't bring himself to return the sentiment. She's furious and storms out.
- The Loins Sleep Tonight: Charlie gets a second chance with Colleen, but a prior conversation with Rose about how his issues with women likely stem from his mother cause him to see her as her mother, and he can't sexually perform.
- Take a Third Option: Jake is getting really good cupcakes at school from a girl that he doesn't like. Charlie tells him that it's okay to enjoy cupcakes without liking the person who gave them to him. Alan tells him he shouldn't take cupcakes from a girl he doesn't like. Jake decides to start liking her so he can keep getting cupcakes.
- Through His Stomach: Robin gives Jake cupcakes at lunch in order to indicate her interest in him and try to get him to reciprocate. He does, although he admits that it's only because the cupcakes are so good rather than him actually liking her. Cupcakes, of course, are being used as a metaphor for sex.
