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When Charlie and Alan take Jake (with a new hair cut!) for pizza, they run into Gail (Tricia Helfer), Chelsea's best friend. Charlie ends up sleeping with Gail just before he gets a phone call from Chelsea, who's having a miserable time in Mexico with Brad. Charlie and Chelsea end up meeting for coffee and they decided to get back together. In the spirit of honesty, Charlie tells Chelsea about Gail, who dumps him. Chelsea comes back over to Charlie's to apologize, only to find Gail there again, sending her to storm off.
Meanwhile, Alan starts picking up a little extra cash by giving an older red head (Frances Fisher) the female equivalent of a rub-and-tug. Eventually, he starts to feel scummy and eventually cuts out the money portion, but seems to continue the rest.