"Oh, Dee... It looks like we both need things from each other."
— Charlie
When Frank decides to start dating again, Barbara seduces Mac in order to get back at him. Meanwhile Dennis threatens to sleep with the Waitress unless Charlie starts doing the dirty jobs in the bar again, and Charlie retaliates by enlisting Dee's help to create a web of lies and backstabbing that will help him get with the Waitress.
This episode provides examples of the following tropes:
- All Love Is Unrequited: Charlie loves the Waitress, who hates him but loves Dennis, who couldn't care less about her but is willing to use her to manipulate Charlie. Also, Mac develops an unrequited crush on Barbara, who was just using him to get at Frank.
- Blackmail: Dennis threatens to have sex with the Waitress unless Charlie agrees to give him his old job back.
- Break the Cutie: By the end of the episode, the Waitress is so traumatized that she ends up sleeping with Frank and delivers an increasingly unhinged Motive Rant to Dennis.
- The Chessmaster: Charlie, surprisingly enough, manages to effortlessly manipulate all of his friends and set up an intricate web of lies, all to get the Waitress to go out with him. It almost works, too.
- Continuity Nod:
- Charlie is now manager of Paddy's while Dennis and Dee are still stuck doing "Charlie work" after the events of the previous episode.
- Mac states that he's had to "make adjustments" in a sexual relationship before.
- Didn't Think This Through: Charlie admits to Dee he didn't think about the possibility that his mom might actually sleep with Dennis when Dee asks Charlie how he knew his mom wouldn't sleep with Dennis.
- Dirty Old Man: While out with a woman he dated in high school, Frank spends most of the time checking out the young waitress and decides that his date is too old for him (despite her pointing out that she's actually two years younger than he is). He later tries to pick up young women at the bar, and eventually has sex with the Waitress.
- Dress Hits Floor: Used in the cold open, when Barbara drops her robe to the floor to seduce Mac.
- I Banged Your Mom: Mac bangs Dennis's mom. And then Dennis tries to bang Mac's mom and later Charlie's mom as revenge, but fails, and the Waitress bangs Dennis's dad.
- Inferiority Superiority Complex: Getting rejected by both Mrs. Mac and Mrs. Kelly in succession crushes Dennis's ego to the point where he's in tears.Dennis: (sobbing) I am an attractive man!
- Likes Older Women: Charlie and Dee manipulate events to make the Waitress think that Dennis is this by ensuring that she's there to witness his attempted seduction of both Mrs. Mac and Mrs. Kelly. Mac also develops a genuine fetish for older women as a result of his fling with Barbara in this episode.
- Manipulative Bastard: Dennis has no problem using the Waitress as a pawn to manipulate Charlie and even goes as far as telling her he loves her to get her to sleep with him.
- Mrs. Robinson: Subverted with Barbara, who seduces Mac but states that she was only doing so to get back at Frank and that she doesn't actually find him attractive.
- Retired Badass: Angie used to get into all kinds of wild shenanigans when she dated Frank back in high school, but then she settled down and started a family. Frank, who was hoping to pick up where they left off, is extremely disappointed.
- Romantic Wingman: Frank forces Mac to act as this for him when he tries to pick up younger women in the club.
- Sexual Extortion: When Charlie tells Dee that they both need things from each other, she initially thinks he's propositioning her in exchange for his getting her out of doing Charlie work. She later tells Dennis that this is what he's doing, as a part of their long game.
- Skewed Priorities: When Dee tells him that Charlie is extorting her for sex, Dennis's reaction is to complain that he's the only one not getting laid.
- Suddenly Shouting: Charlie does this while on the phone with Dee:Charlie: Time to move to Phase 2.
Dee: There is no Phase 2! I'm not doing Phase 2, I did everything you said, and it's over.
Charlie: (screaming into the receiver) THIS ISN'T OVER UNTIL I SAY IT'S OVER!!! - That Came Out Wrong:Charlie: It's not sex I want from you... It's sex I don't want from Dennis.
Dee: Hmm? - Wimp Fight: The fight between Mac and Dennis, which starts with Dennis slapping Mac's face and ends with the two of them wrestling pathetically on Barbara's lawn.
