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.
When a former owner of Angela’s home stops by to make an enormous offer on the place, Tony convinces Angela to accept the offer so they can begin searching for what he thinks will be the perfect place to call their own. However, when they find out what he plans to do with the house after he buys it; Tony and Angela decide to back out of the deal.
Due to financial expenses at the Bower Agency; Tony, Angela, and the rest of the family are forced to cut costs at home. While the others are adjusting to the tighter purse strings, Angela is having a hard time and eventually goes on a shopping spree. When Tony discovers what she did, he forces Angela to hand over her credit cards.
After meeting his successor on the St. Louis Cardinals, Tony has a dream of what his life would have been like if he didn’t injure his shoulder. After seeing how unhappy he and everyone around him are with their lives if he was a famous baseball player, Tony starts to long for how things were before.
After frequent instances of swollen lips, Tony enlists the help of Samantha, Mona, and Jonathan to discover the cause. Despite Tony’s repeated insisting that he is allergic to something in the air, Angela begins to suspect that Tony isn’t ready to get married because his lips always begin to swell when they discuss their wedding.