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.
Chelsea regrets having convinced Vidal to serve as coach of Shavonne's Pee wee league basketball team when Vidal turns into the coach from hell.
Jeff finds a wrench has been thrown into his ""five-year"" plan for life when he unexpectedly falls in love with a woman ahead of his ""schedule.""
On the eve of her birthday, Chelsea finds herself nostalgic for the adulation and ovations of the concert crowds. Should she give up the club and head back out on the road?
When Jeff and Vidal's old friend—a successful businessman, who's also a suave ladies man, comes into town for a visit, the guys are eager to hear more of his legendary romantic conquests. But Vidal and Jeff's eagerness turns to horror when they discover their friend's next target is Charisse.
When Vidal spots Hilary Banks at the club, it's lust at first sight. Intent on landing her, Vidal asks Charisse to do a little spy work on his behalf. When he discovers Hilary is sick of dating vain, superficial and immature ne'er do-wells, Vidal passes himself off to Hilary as a successful businessman who's manager of the club. When Chelsea discovers the ruse, she decides to teach Vidal a lesson by forcing him to run the club on the night of his date with Hilary.
In an effort to establish their status as adults, Vidal, Jeff and Angus decide to spend Christmas on their own and away from their families. However, the boys soon regret their decision when the ski trip they've planned turns into a disaster.
As Chelsea's hectic life on the road begins slowing down, she realizes a void that's been missing in her life: love. And thus Chelsea begins her first tentative steps into the dating scene.
Jeff once again finds himself trying to escape from his father's shadow when the over-achieving disciplinarian visits his son.
Charisse is in heaven when she not only gets a job as a stylist for a music video, she convinces the director to shoot the production at the club. But Charisse's dream soon turns into a nightmare when the director hires Vidal as a production assistant.
It's a bittersweet high school reunion for Chelsea when her old friend, who in many ways has more talent than Chelsea, shows up, jealous over her friend's success.
Vidal finds himself without a place to live when Jeff becomes fed up with his roommate's living habits.
When the gang is convinced that Vidal can't stay with one woman for a week, Vidal sets out to prove them wrong. However, the V-man's patience is truly tested when his new girlfriend turns out to be an incredibly pushy woman.
Vidal realizes his friendship with Shavonne has unexpected benefits when the little kid turns out to be a girl magnet. When Vidal tries to exploit the situation, Chelsea and the gang decide to teach him a lesson.
Charisse finds herself in the uncomfortable position of being romantically pursued by her boss. In an effort to deter his advances, Charisse claims her boyfriend is .... ahem.... Vidal.
Charisse is thrilled to spend some quality mother-daughter time with Chelsea when the diva decides to plan a party for the building. But Charisse soon becomes jealous when Chelsea begins relying on Jeff's expertise rather then Charisse's in setting up the shindig.