Jake gets dumped by his girlfriend, which causes Alan to reminisce about his high school girlfriend, Charity Kirshenbaum, who dumped him on prom night. On finding out that she had dumped him for Charlie, Alan sets out for revenge.
Tropes
- The Bad Guy Wins: Calling Charlie the 'bad guy' is a little much, but he did steal Alan's high school girlfriend back when the two were younger, and when Alan finds out and seeks revenge, Charlie manages to manipulate the whole situation so he gets exactly what he wants, and even twists the knife by hooking up with Alan's high school girlfriend again.
- For Want Of A Nail: Alan genuinely feels that his entire life would have turned out much better if Charity Kirshenbaum hadn't dumped him on prom night, and on finding out that Charlie stole her from him blames him for it.
- Lousy Lovers Are Losers: Averted. Gabrielle is beautiful and seems like a perfectly nice person. It's just her idea of sex is to lay down lifelessly on the bed and let the guy do all the work.
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Magnificent Bastard: Charlie is dating a beautiful French woman named Gabrielle who is awful in bed, and wants to dump her. After Alan finds out that Charlie stole his high school girlfriend twenty years ago, Charlie anticipates Alan seeking revenge and arranges for Alan and Gabrielle to be left alone for awhile so Alan has an opportunity to steal her away from him. He does so, but Charlie immediately manages to make Alan feel incredibly guilty for this, meaning he can't even enjoy his revenge. Then, Alan has 'sex' with Gabrielle, and realizes that Charlie wanted to end the relationship, and all Alan accomplished was giving him a guilt-free and fault-free way out. Oh, and when Alan heads home, Charlie is in the middle of bedding Alan's high school girlfriend. - Took a Level in Jerkass: Compare this episode to a season two episode where Charlie realizes something he did as a kid had an extremely negative effect on Alan. In that episode, Charlie felt awful and confessed to it out of guilt, and then tried to find some way to make it up to Alan. In this episode, he tries to hide the truth, then tries to marginalize and trivialize what he did, and then manipulates Alan so that his attempt to get revenge just ends up serving his purposes, and then sleeps with Alan's high school girlfriend just out of pettiness, as if he was the one who needed to get revenge.
