Who's the Boss?

Tony Micelli, a single father, moves with his sharp-witted daughter Samantha from a tough urban neighborhood to Connecticut in search of a better life. He accepts a live-in housekeeper position with wealthy businesswoman Angela Bower and her son, arranged through Angela's flirtatious mother, Mona. The arrangement leads to the formation of an unconventional new family.

Tony accidentally sees Angela while she is in the bathtub, leading to tension between the two housemates as they refuse to take responsibility for the situation. Their conflict escalates to the point where Tony's new girlfriend ends the relationship. With Mona's guidance, Tony and Angela use role-playing to gain insight into each other's perspectives, ultimately realizing their anger was misplaced.

Angela accompanies Tony to his former neighborhood in search of the runaway Samantha, defending him when he faces criticism for working as a housekeeper. Despite her insistence that arguments are not the solution, Angela becomes involved in a physical altercation with a waitress at one of Tony's old haunts.

Mona begins a relationship with Jason, a much younger man, leading to family tension when the age difference is revealed. Angela, who initially supports love regardless of age, is shocked by the relationship. However, after Jason's parents criticize Mona, Angela reverses her stance and defends her mother.

Tony visits Angela at the set of a soap commercial and unexpectedly becomes the ad's new star. He later develops a rash caused by the product, forcing Angela to consider whether to continue promoting a soap with potentially misleading claims and harmful effects.

Tony looks forward to a dinner date in Brooklyn as Angela prepares for a business dinner with a client. When Angela's guest cancels last-minute, Tony agrees to stay in Connecticut with her, postponing his date.

A college friend of Angela's visits and becomes interested in Tony, creating tension in the household.

Tony and Angela find themselves in a case of mistaken identity when they each pick up a date who believes they are someone else. As the misunderstandings escalate, both are forced to address the growing complications with their deceived partners.

Angela begins a relationship with a man who is deeply passionate about sports. However, he spends more time with Tony, engaging in sports discussions, than he does with Angela.

Tony is working extra shifts to earn more money, leading Mona to suspect he's hiding a secret girlfriend in Brooklyn. It is later revealed that Tony is actually covering the rent on his late father's apartment as a backup plan for him and Sam if their move to Connecticut doesn't work out.

Tony helps Samantha buy her first brassiere, but when it doesn't meet her expectations, he asks Angela to help find more suitable clothing. Tony becomes uneasy when Samantha returns home looking more mature than he anticipated.

Angela wants to paint the family's Jaguar sandalwood, but Tony disregards her choice and has it painted diablo red instead. Upset by his decision, Angela bans him from making future decisions and mocks him as just the maid. Taking her words literally, Tony begins acting like a formal, over-the-top butler.

At a company party held at Angela's home, Tony takes disciplinary action by dismissing one of her vice-presidents after he makes inappropriate and unprofessional remarks about her.

Mona, after being evicted, starts searching for a new place to live and decides to take Tony's advice to turn the loft over Angela's garage into a residence. Angela is resistant to the idea, creating tension between the two.

Angela's ex-husband, Michael, comes to finalize their divorce, but they end up reconnecting and rekindling their relationship. With Michael returning to their home, Tony, who had been living there, is informed he must leave within two weeks.

Tony and Samantha attend a party at the opulent home of Tony's influential new employer, while Michael and Angela reconnect after time apart. However, underlying tensions resurface, highlighting the issues that initially caused their separation.

A local news reporter, Bobbi Barnes, seeks to document Angela's everyday life, but a series of misunderstandings results in Tony and Angela being found together in bed, with Bobbi's crew ready to film. Bobbi believes she has uncovered a compelling story, though Mona has different plans.

Samantha is excited about the school dance, but her evening is disrupted by Tony, who takes numerous photos of her and her date, serves as a chaperone, and causes a scene by being caught kissing her teacher in front of classmates.

Nick, Tony's father-in-law, visits the family and falsely claims he is dying to avoid confessing that he will soon be going to prison, using the situation to gain sympathy from those around him.

Jonathan begins to emulate Tony's rebellious behavior, prompting Angela to assert her authority by insisting on being involved in all decisions about her son's future. Determined not to be overruled, Tony takes matters into his own hands to resolve the situation.

Tony struggles to afford Samantha's ski club membership, initially allowing her to join but later having to withdraw his support after a failed attempt to save money backfires. Determined to fulfill his promise, he refuses financial help and instead sells a personal treasure to cover the cost.

Angela returns home after attending a lively birthday party, while Tony comes home following a police demonstration on the effects of alcohol. Both are disoriented and end up sharing a kiss.