Jeff Carswell and Vidal Thomas have hit the jackpot. Fresh out of school, Jeff's not only landed a dream job as the manager of a hot nightclub owned by singing star Chelsea Paige, but she's also provided both young men with an apartment in her own building. Vidal's in heaven too. The club provides the perfect setting for this ""lady's man"" to pick up women. But the dream's too good to be true. Paige turns out to be a maternal figure who keeps a constant and watchful eye on not only Jeff and Vidal, but also her over-protected and beautiful daughter who's befriended the two men.

In the interests of keeping their friendship intact, Vidal and Jeff make a solemn oath to each other that neither man can ever ask out Charisse. But when Charisse goes on a tirade against men after getting dumped by her latest boyfriend, Chelsea, in an effort to show her daughter that all men are not scum, urges Jeff to take her daughter out on a date. When Vidal finds out about the rendezvous, sparks fly between the two best friends when Vidal accuses Jeff of betrayal.

Vidal's found the perfect playmate. Like Vidal, he's fun-loving, irresponsible, and emotionally immature. Best of all, he lives in the building. Unfortunately, he's also six years old. No matter—Vidal and little Shavonne begin spending all their time together. But Vidal finds his carefree relationship with the boy turns out to be more than he's asked for when Shavonne asks him to be his official sponsor in the Big Brother's program.

Eager to escape from the shadow of her mother, Charisse accepts a great job opportunity in New York. A panicked Chelsea tries finding a way to keep her daughter from moving by setting up an equally attractive job for her in L.A. Chelsea uses a reluctant Jeff to help ""trick"" Charisse into staying. Charisse falls for the scam. But Chelsea and Jeff soon find themselves wracked by guilt over their deed and both admit their actions to a furious Charisse.

Chelsea's feeling guilty when her longtime musical director has nowhere to go now that she's stopped touring. Desperate to find him work, Chelsea has Jeff hire the man as an assistant. But to his dismay, Jeff soon finds out the man is long on charm but short on organizational skills. Forced to let the old man go for incompetence, Jeff discovers hell hath no fury like a boss who's discovered an old friend has been fired.