Ben está em seus 20 anos e, de repente, ele se torna pai quando um bebê é deixado na porta de sua casa pela sua ex-namorada. O rapaz então decide cuidar da garotinha, com a ajuda de sua mãe, Bonnie, seu irmão, Danny, seu melhor amigo, Tucker, e sua amiga, Riley, que tem uma paixão secreta por ele.
A grumpy Ben wishes there was no such thing as Christmas, then is shocked when the fulfillment of his desire not only erases the holiday, but Emma's existence as well.
Tucker enlists Ben and Riley to appear on Mary Hart's program and reveal how they foiled an attempted mugging; Bonnie hopes to get rich by using Emma in a series of Internet videos.
Danny receives a cameo role on "General Hospital" and nervously prepares for his scene with actress Kelly Monaco; Tucker and Ben stage a funeral for Bonnie.
Ben panics when he forgets his mother's birthday; Danny learns surprising news that overshadows Bonnie's party; Emma is injured while in Riley and Tucker's care.
Emma's babysitters feel unappreciated, so they go on strike, forcing Ben to bring Emma along on his dates and shifts at work. Meanwhile, Danny and Bonnie enroll in a cooking class with her favorite chef; and Tucker tells Riley to invent a fake boyfriend.
Ben and Riley make a bet concerning strangers in a bar and it leads to trouble at work for both of them: Riley sleeps with a stranger who becomes her new boss, and Ben sleeps with the wife of the man who's trying to purchase the bar where he works.
Tucker hires Riley to represent him in a lawsuit against a construction company, but his hazy memory makes the case challenging for her. Meanwhile, Bonnie predicts her sons will fail as bar owners, and she attempts to hasten the demise of their business.
Ben corrupts Ross by spending too much time with him, which infuriates Riley and leads her to declare a war in which Ross—unbeknownst to him—is the prize. Meanwhile, Bonnie wants to join the guys' poker game.
Riley hosts a cocktail party in order to meet Ross' friends, and Ross tells Ben not to attend. Meanwhile, Danny tries to figure out his new girlfriend's last name; and Tucker starts divulging secrets after he has too much to drink.
In the Season 4 finale, Bonnie's wedding planner quits as her big day draws near, so her best buddy, Charlotte, volunteers to help, but Charlotte has an ulterior motive. Meanwhile, Ben decides to let Danny and Riley have a shot at romantic happiness.
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