Maestro's suave, career-minded older brother Jared must break the news of the ""arrangement"" to his carefree, aspiring musician roommate Sean. Needless to say, Sean is less than thrilled with the news that a six-year-old child is his new roommate and questions the impact Maestro's presence might have on his sex life. But it's not long before Sean realizes Maestro's ""babe magnet"" potential, and he quickly learns to use his adorable pint-sized roomie's charm and wit to his advantage.
When a gorgeous young woman moves into the guys' apartment building, Sean is instantly smitten and offers a neighborly hand in getting her settled. The two begin spending time together, leading Sean to believe that he's ""so in there."" But Kara doesn't like Sean because he's ""in,"" but rather because he's ""out""-- of the closet, that is. She's mistaken Sean and Jared for a gay couple raising a child.
Maestro develops a big crush on his babysitter Katie, a precocious 13-year-old who's more impressed with older musicians, especially Sean. Meanwhile, Jared tries to learn golf to impress his boss Mr Levin, who happens to be Katie's father.
When Maestro lands the lead role of Peter Pumpkin in his school's annual ""parents please participate"" Halloween pageant, he assumes that his big brother Jared will play Papa Pumpkin to his Peter. But Jared's on the verge of a promotion at work and must choose between climbing the corporate ladder or upholding a commitment to family.
Sean announces he's moving out after his band loses a gig because having to baby-sit Maestro prevented them from recording an important demo tape. Meanwhile, Jared's having his own problems at the office, developing an acceptable marketing pitch.
When Jared agrees to let Maestro star in a new ""Daka"" national sportswear commercial, Sean volunteers to supervise Maestro on the job so that he can convince the director to use his band's music for the commercial. But Jared, trying to make quality time for his out-of-town girlfriend, sees Maestro and Sean having to much fun together and feels left out.
When Maestro asks questions about ""the birds and the bees,"" Jared and Sean pour through books on how to communicate with children then each take a stab at answering some of the seven-year-old's question's - but only succeed in confusing him more.
Jared and Maestro plan to observe Thanksgiving eating pizza and watching football---until the kid learns that his teacher is spending the holiday alone, and invites her to join them. While Jared and Sean clumsily scramble to cook a traditional turkey dinner for their guest, Maestro searches for the true meaning of the holiday.
To prove to Jared that women love foreign men, Sean does his best Scottish impression for Audrey, a woman he notices at the bar. To everyone's surprise, including Sean's, Audrey falls for the Scotsman bit and their relationship blossoms. That is, until Sean's co-worker Jude introduces them to Gavin - her real Scottish friend.
Maestro and Nikki get into all kinds of trouble when they go on an on-line shopping spree with a gold credit card that came in the mail. The two have good intentions when they purchase gifts to cheer up Jarod and Sean (including hundreds of Sean's non-selling ""Rock the Hat!"" CD), but they end up learning a lesson in responsibility.
Sean and Jared both lose trust in each other when Jared's ex-girlfriend, Jennifer, shows up and begins dating Sean. Later she makes a move on Jared, but luckily, Maestro captures Jennifer's deviousness on videotape and it becomes clear that she is only using Sean to get back with Jared.
Jared and Sean are psyched to see their old college buddy, Steve ""The Fig"" Figgison, but are quickly stunned when their favorite party guy rolls into town with some big news -- he's settling down and getting married. However, it only takes one night out on the town for Steve to call off his wedding and question whether or not he'd make a good parent. Sean and Jarod know Steve's making a big mistake so they set out to set him straight.