After Evelyn's new beau dumps her, Charlie and Alan enlist Jake to cheer her up; Charlie teaches Jake a lesson about screening telephone calls from women.
Tropes:
- Cool and Unusual Punishment: Alan punishing Charlie by tricking him into playing the piano for their mother's song and dance medley.
- Flirty Stepsiblings: As they locate their missing mother, Alan points out that if she did marry her boyfriend, that would be great. The only downside is that Charlie will have already slept with their new stepsister Olivia. Charlie finds that idea sexy while Alan appropriately calls it sick.Alan: If they did run off to get married, great! The only downside would be that you slept with our stepsister.Charlie: Huh. Haven't thought of that. Kinda sexy.Alan: Kind of sick.Charlie: I'm saying!
- Girl of the Week: Amy (off-screen) and Olivia for Charlie.
- Guy of the Week: Tommy for Evelyn.
- Hypocrite Evelyn telling Charlie that her breakup with Tommy has nothing to do with his involement with Olivia and calls him "a narcissist". Then she bemoans about Tommy leaving her for a younger woman.
- It's All About Me: Evelyn moping about her breakup from Tommy.
- It Meant Something to Me: Evelyn is distraught when her ex Tommy has moved on so quickly, questioning if she meant that little to him.
- Kick the Dog: During an argument with his neglected ex Olivia, Charlie tells her "I said you were special, not unique.", causing her to throw her drink in his face and storm out angry.
- May–December Romance: Implied when Evelyn complains that Tommy left her for a "fresh-faced 45-year-old bimbo".
- New Old Flame: Olivia, who Charlie dated years ago. She thought it was exclusive while Charlie was cheating on her with three other women.
- Nice Job Breaking It, Hero:
- Evelyn's reaction when Charlie ruins her dinner party by insulting her beau Tommy's daughter Olivia.
- When Charlie sympathizes with his mother and tells her he loves her, Evelyn goes to pack her bag and leave to go home. Charlie asks why. Evelyn tells Charlie that he just said he loved her and that he could only screw it up from there.
- Oh, Crap!:
- Charlie, when he sees his ex Olivia who just happens to be the daughter of the new guy Evelyn is dating.
- Evelyn when she learns that Charlie had already slept with her new boyfriend Tommy's daughter Olivia in the past.
- Evelyn and Tommy's reactions when Charlie insults Olivia.
- Papa Wolf: Tommy follows after his daughter Olivia after storms out from being insulted by Charlie.
- Really Gets Around: Evelyn calls out Charlie on his philandering when she's shocked to discover that he's already slept with her new boyfriend's daughter Olivia in the past.Evelyn: Is there anyone in the 310 area code that you haven't mounted?
- Screw This, I'm Outta Here:
- Tommy immediately follows after his daughter Olivia after she curses Charlie for mistreating her and tossing a drink in his face.
- Jake immediately takes off running back to his room after having to spend time with his depressed grandmother.
- After Charlie tells her he loves her, Evelyn decides to packs her things and go home.
- Shout-Out:
- Charlie asking Alan if he checked with the captain of the flying monkeys.
- Evelyn's piano song and dance medley consists of songs from Nancy Sinatra's "These Boots Are Made For Walking", James Brown songs and Dean Martin songs (the last of which are played offscreen).
- Jake shouts "Donkey Kong!" when woken up from his sleep during Evelyn's piano medley.
- Unwitting Instigator of Doom: Charlie gets into an argument with, and insults, his ex Olivia, who just happens to be Evelyn's latest boyfriend Tommy's daughter, shortly after which Tommy breaks up with Evelyn.
- This Is Gonna Suck:
- Evelyn let's out an "oh no..." when she figures out that Charlie already defiled Tommy's daughter Olivia.
- Evelyn and Tommy's reactions when they hear Charlie tell Olivia "I said you were special, not unique".
- Charlie and Alan when they hear Evelyn bemoaning in her depression before taking a few steps out of her house.
