Charlie and Jake convince Alan to get a makeover when it appears Judith is moving forward since the breakup, sporting a new hairdo and new date. Alan realizes he may truly be in need of a change when his own son tells him he doesn't look cool. But when Charlie takes Alan shopping, the brothers clash over what image is right for him. Meanwhile, highfalutin Evelyn remains at Charlie's house to bond with her grandson, Jake.
Alan organizes a family dinner to celebrate the publication of a newspaper article that describes him as a "good doctor, good neighbor and a good guy," but he's crushed when his mother, Evelyn, isn't impressed. After getting drunk, Alan experiences a life-changing epiphany and vows to a skeptical Charlie that he is no longer going to grovel for validation from his mother and the other women in his life.
Charlie agrees to meet with a former girlfriend who ended their relationship years earlier, leaving Charlie devastated. But Charlie's in for a huge surprise when he discovers that she is now a he, and he, Bill (CHRIS O'DONNELL - "Batman & Robin"), wants to be Charlie's friend. Initially disturbed by the sex change revelation, Charlie relents and befriends Bill. But Charlie and Alan are horrified when Bill starts dating their mother, and Evelyn becomes sexually intimate with Charlie's ex-girlfriend!
While Alan and Jake are away on a road trip, Charlie is visited by the ghosts of his ex-girlfriends.
When Rose announces that she is moving to London permanently, Charlie doesn't listen at first. But he eventually realizes that he must face his true feelings for her. Meanwhile, Alan tries online dating--with unforeseen results. After exaggerating while writing his profile on an internet dating service, Alan attracts a fellow profile embellisher, Beverly (ALLISON JANNEY - "The West Wing").
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