When Jake is dumped by a girl for the first time, Alan tries to make him feel better by talking about the first time he was dumped. It was in high school and the girl, Charity, dumped him the night before a big dance. Charlie's advice to Jake is to find the prettiest girl, because the prettiest ones are the loneliest, and ask her out because all the other guys will be afraid to. Later, Alan has a drink or two and starts reminiscing about Charity and wonders why she dumped him. He pulls out his old year book and decides to call her. Charlie tells him nothing good can come from drunk dialing an old girlfriend. Alan reaches Charity on the phone and asks her why she dumped him right before the dance. She tells him to ask his brother. The next day, Jake takes Charlie's advice and asks out a pretty girl. It works: she says yes. Meanwhile, Alan can't stop giving Charlie a hard time about stealing Charity, but Charlie doesn't think twice about it and leaves. Gabrielle, Charlie's current flame, drops by looking for Charlie who hasn't been answering his phone. Alan seizes the opportunity to bond with her emotionally and they set up a date. Charlie comes home and sees the two of them hitting it off on the porch. He puts a horrible guilt trip on Alan, but eventually says that he should continue dating Gabrielle. A vindicated Alan goes out with Gabrielle, but when things become intimate she lies on her bed like a robot and tells him to get it over with. Alan realizes that Charlie wanted to get rid of Gabrielle all along and had him do his dirty work. Making matters even worse for Alan, Charlie connects with ex-girlfriend Charity a second time.