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Original Air Date: April 28, 2008
The title comes from a story that EVELYN tells COURTNEY (Guest Star Jenny McCarthy) about ALAN in the opening scene to embarrass him, which is exactly what it does. When he was a young boy, Alan apparently liked to play dress-up with his mom’s makeup and clothing, and she claims he would always run and tell her, “Look at me, mommy, I’m pretty.”
CHARLIE comes downstairs after his mother gets through with her revelation, and when she leaves the room, he isn’t too happy when Alan tells him and Courtney they mustn’t let Evelyn know they’ve been fooling around. Alan is playing wedding planner, and he’s intent not to ruin Evelyn’s fifth wedding. Charlie’s mood gets even worse when Courtney agrees with Alan because she doesn’t want to mess up the good relationship she’s finally enjoying with their mother.
At a family dinner with both families later, TEDDY (Guest Star Robert Wagner) reveals he loves Evelyn so much he doesn’t even want her to sign a prenuptial agreement. Not that it makes any difference since, as Alan and Charlie learn when they overhear her talking to Courtney, she has enough money of her own already.
Money or not, Charlie remains obsessed with Courtney because he thinks she’s a female version of him. As he sits outside her apartment that night stalking her, his own stalker, ROSE, shows up to give him a few supplies: a bottle of water, trail mix, and a pee jar. She then heads off to begin stalking Teddy after he comes out to the car to confirm that Charlie and his daughter are going to stop seeing each other so Evelyn won’t find out and think he knew but didn’t tell her.
Regardless of everyone’s efforts to keep Courtney and Charlie’s relationship a secret, the pair end up back together anyway when Courtney has a heated argument with Teddy over his refusal to help her keep her condo when she loses her job. Charlie visits Courtney at the apartment and offers to lend her the $50,000 she needs. She accepts, and later at their parents’ wedding, Charlie asks her to marry him by silently mouthing the words while Teddy recites the long-winded vows Evelyn wrote for him. Courtney mouths back that she will.
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