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.

The family visit Jonathan's summer camp when his counselor calls Angela to say he is homesick. While there, Angela and Tony realize they both attended camp in the same area many years earlier. Their individual stories of their first kiss seem to coincide, and they soon suspect they may have met each other a long time ago.

After visiting the site in the woods where each remembers from their past, a thunderstorm prevents Tony and Angela from returning to the campsite in time. They end up having to share a room at a cheap hotel. Meanwhile, Mona and the campers tell scary stories and play pranks on the counselor.

Samantha has just begun junior high school, and has little trouble becoming friends with the popular girls. Since they are all from wealthy families, Samantha is afraid they will not like her if they know of her true past, so she tells them that Tony owns Angela's house and is an advertising executive.

Overworked Angela goes to Mexico with the family, but when Angela's business loses an important account, Tony never gave Angela the message. When Angela comes home, she goes to the agency to learn that they lost the account. After sassing to her boss and telling him to chill, Angela loses her job.

Angela tries desperately to find a new job but no one of her old friends or partners has one for her.The only job she can find is one of a copy writer.Eventually,Tony and Mona convince her to open her own agency.

Marci applies for the elite-school Montague. Sam also wants to do so and finds an advocate in Angela, a Montague Academy graduate. But Tony doesn't like the idea that Sam visits a school so far away.

At a street carnival in Brooklyn Tony and Angela help at Mrs. Rossini's stand. There Tony also meets Frankie, an old friend. At an charity auction - Tony offers his services for a weekend - she makes the race.After the weekend Tony returns with a proposal from Frankie.

Sam has found a new friend and meets him at the library. But it's the college library - Tony finds this out and assumes that her new friend must be much too old for her. Immediately he goes there and in front of everyone he makes Sam look like a fool. Sam's friend is the 15 year old genius Mason whom Sam just want to use to show off in front of her friends.

Angela and Tony want to pair off Angela's cousin Christy and Tony's friend Lyle. The evening together didn't go as planned, but on the following day the both stand in the doorway announcing their wedding. But unfortunately the wedding coincides with an icehockey game. As the game is more important, Christy angrily cancels the wedding.

Young Samantha has reached a teenage milestone - she has her driver's license! But in upscale Connecticut she feels left out when Bonnie gets a brand new car but Tony buys Samantha a hazard light on wheels! It comes down to pride vs love when it's discovered she's parking blocks away from her school.

In an effort to better himself, Tony heads off to college. The public speaking class is headed up by a strict grammer enthusiast who singles Tony out as an impossible case. Its My Fair Lady as Tony does a complete turnaround, but he alienates himself from his family and friends and must rely on the ""inner Tony"" to figure out who he really wants to be.

Tony has been invited to a frat party and Angela accompanies him. But there Angela drinks a little too much of the (with alcohol mixed) bowle and 'entertains' those present. In the end Angela and Tony land up in the campus jail.

Holidays on Jamaica. And everyone enjoys the life there.Angela, too, dives right into the holiday-action and has a lot of fun. As it's not Tony, with whom she has that fun, he gets jealous.

Charlie, Sam's female friend from Brooklyn, visits while Angela is preparing for a dog food commercial. Charlie talks Sam into ditching school for the day and going to the beach, but Tony catches them before they leave the house. When Tony calls Charlie's mother to tell her, he learns that her mother doesn't care about Charlie and doesn't want her in her life.

Tony and Angela are apartment-sitting for Mrs. Rossini. After meeting two couples Tony used to be friends with, Angela dreams that she and Tony are married, living in Brooklyn, and expecting a baby.

Angela meets, and begins to date, Christopher, a man who appears to be perfect. Everyone who meets him seems to feel as if they've met an angel. Tony, however, cannot seem to meet him, encountering several failed attempts, which begin to ruin his relationship with Kathleen.

Sam has spent the summer working at a ranch in New Mexico. When she calls home and announces that she'd like to move there permanently, Tony and the family fly out to change her mind. Tony is adamant that she return to Connecticut and go to college, but even more so when she meets her new boyfriend.

Discouraged that Angela is spending too much time at home, Tony convinces Mona to bring her to a night club. Angela does loosen up, but more so than Tony had intended. Soon, Angela is having middle-of-the-night parties, skipping work, and becoming a regular at Mona's club.

Angela is ready to profess her love for Tony, but her hopes for a romantic anniversary night with him are dashed when he invites her and the whole family to a carnival. A fortune teller tells Tony that he is about to lose the love of his life, but he misses the point. A ride through the Tunnel Of Love changes their relationship.

After Tony and Angela have confessed their love for each other,they both now want to spend an enchanting evening together.But that isn't that simply,especially since no one can know about it.

Tony, like it's always his way, overdoes his relationship with Angela. But Angela doesn't dare to tell - and tries to get out of his way.