Who's the Boss?

Single dad Tony Micelli and his street smart young daughter Samantha decide to leave the mean streets of their poor neighbourhood for a chance at a better life in Connecticut. Tony happens upon a job offer as a live-in housekeeper for wealthy business woman Angela Bower and her young son by means of her flirtatious mother Mona. He puts his machismo aside and takes the job for the betterment of his daughter and a new ""family"" is formed.

Part of settling into his new home has Tony using Angela's personal bathroom and getting an eyeful when she steps out of the tub. Neither of the two stubborn housemates accept responsibility, and disagree to an extent that Tony's new girlfriend gives him the heave-ho. Mona's advice about role-playing to better understand each other's point of view helps Tony and Angela see that they aren't angry after all.

During a trip to Tony's old neighbourhood to find runaway Samantha, Angela must stand up for Tony who is criticized for being a housekeeper. After proclaiming that fighting is no way to resolve a dispute, Angela ends up in a cat fight with the waitress in Tony's old hangout.

Mona meets Jason, the man of her dreams, but she's old enough to be his mother! After much hiding the truth comes out and Angela, who previously stated that age had no part in love, is aghast. It's not until Jason's parents tell Angela that Mona isn't good enough for their son that she stands up for her mother and does an about-face of her opinion.

Tony visits Angela at the filming of a soap commercial, and ends up the star of the ad. Soon after, Tony develops an itchy rash that turns out to have been caused by the soap. Angela must then decide if she wants to market a soap whose makers are not completely honest about its potentially harmful side effects

Tony is greatly anticipating his dinner date with a girl in Brooklyn, just as Angela is preparing for a business dinner for two with a client. When Angela's guest cancels at the last minute, Tony reluctantly stays in Connecticut to keep her company, while attempting to keep, but slightly postpone, his date.

Angela's sorotory sister from college comes around and takes an interest in Tony.

At the market, Tony picks up a woman who believes that he is the owner of Angela's house and Jaguar. Meanwhile, Angela accepts a date with a man who believes that she is Rosie, Angela's flighty secretary. Both advise the other that no good relationship can begin based on a lie, and soon both are forced to confront their deceived dates.

Angela becomes involved with a gentleman who is quite the sports fanatic. He becomes more interested in hanging out with Tony and talking sports than in spending time with Angela.

Tony is moonlighting to raise extra money, which Mona believes is to take care of a secret girlfriend in Brooklyn. Soon the truth comes out: Tony is still paying rent on his recently deceased father's apartment, so that he and Sam will have a place to go just in case things don't work out in Connecticut.

Forced to confront the fact that Samantha is not a little girl any more, Tony buys her her first brassiere. When it turns out not to be the kind she wanted, Tony enlists Angela's help in buying Samantha new clothes. He is less than thrilled, however, when Samantha comes home looking a bit too grown up. (Note: This episode was originally titled ""Samantha's First Bra"" but was later changed due to censoring problems.)

It's time to paint the Jaguar, and Angela wants the new color to be sandalwood. Tony overrides her decision and has it painted diablo red. When Angela discovers this, she is enraged and forbids him from future decision-making, proclaiming that he is just the maid. He then takes this declaration to the extreme by dressing, speaking, and behaving like a prim and proper butler.