Kirk's middle-aged landlady sympathizes with her tenant but has no intention of helping Kirk, while his gorgeous neighbor, third-year medical student Elizabeth Waters, prefers to ignore Kirk's romantic advances in favor of her medical books. Extricating himself from the scheming antics of his pal, Eddie Balducci, Kirk gamely struggles to find time for his own life.

In an effort to prove that he can attend to all of the needs of his brothers and sisters, Kirk buys Phoebe her first brassiere. When he presents it to her with her siblings and friends watching, she is extremely embarrassed. Phoebe plans on moving in with Elizabeth, but Kirk desperately tries to get her to forgive him. He tells her some embarrassing things about himself, such as knowing all of the words to the theme song for the television show Full House. Phoebe plots her revenge with this knowledge.

Kirk decides not to make Corey baby-sit for his younger siblings because Corey has a special homework assignment. But with no one to care for them, Kirk is forced to bring Russell and Phoebe with him on his first date in New York City. The kids get tickets for a children's movie next door to the movie theater where Kirk and his date are. While trying to watch the movie with his date, Kirk sees Corey at the same movie with a date. Angry that Corey's not studying, Kirk insists Corey go to the other theater to watch his siblings. Unfortunately, Corey cannot find the kids and interrupts Kirk. They finally realize that Phoebe and Russell have sneaked into the movie where the adults are.

Eddie entices Kirk to help him sneak into a party where Eddie hopes to interest a wealthy investor in his latest invention -- a belt made out of cured meat. Kirk agrees to help because Elizabeth will be there. However, Kirk's romantic hopes are ruined when he sees Elizabeth at the party with an older man. Kirk is angry because Elizabeth told him that she doesn't want to date anyone right now. Kirk returns home to Phoebe, who is baby-sitting Russell for the first time. Unfortunately, Russell's feet got stuck in the couch when he was jumping on it, and Sally had to help free him. However, Sally keeps what happened a secret. Finally, Kirk confronts Elizabeth about her date. Elizabeth tells Kirk that the man with whom he saw her was her boss, whose wife was also at the party. However, Elizabeth still doesn't agree to go on a date with Kirk.

Kirk wants to enter his cartoon drawings in a comic book contest. To finish the work before the deadline, he needs the kids to be quiet and leave him alone. Russell feels neglected when his well-intentioned attempts to help are unappreciated by Kirk. The night before Kirk's drawings are due, Russell accidentally vomits on them. Kirk struggles with his emotions over the lost opportunity and his concern for Russell's feelings.

Corey's good grades land him in an exclusive school for the gifted. Phoebe gets jealous, and then suspicious after Corey tests higher than she does on an aptitude test. Kirk's enthusiasm over Corey's scores convinces him to attend an open house at the same school that's just rejected Phoebe. Even though Phoebe learns the truth about Corey's high scores, she decides to get even by remaining silent and letting Corey battle his wits with the other students at the gifted school.

Russell develops an attraction to his pretty teacher, Leslie Stevens. Kirk tries to tell him to be realistic, but when Leslie asks Kirk out to lunch, Russell gets jealous. Russell gets Elizabeth to take him to the same restaurant as Kirk and Leslie, so Kirk will be jealous of him. Kirk frantically tries to explain the situation to Leslie and Elizabeth, but the women pity Russell and tell Kirk to leave. Meanwhile, after Corey gambles and loses several possessions in a one-on-one basketball game with an expert player, Zack, former junior high school basketball star Phoebe wins everything back for Corey with a few trick shots. Also, Eddie earns money by taking an experimental drug until his face turns fluorescent orange.

It's Halloween, and Kirk wants to make it fun for his siblings. He decorates the house and takes them trick-or-treating. Unfortunately, they find out that New York City is not the best place to go door-to-door asking for candy. After a dismal attempt at an in-house party, Kirk begins to wonder what Eddie will do for his annual Halloween practical joke. When Eddie's joke goes awry, the police arrest Kirk, who is dressed in a bizarre costume. Now it's Eddie's responsibility to get Kirk out of jail.

After Kirk chases a mugger away from a wealthy woman, she showers Kirk with gifts and gives him a chance to meet people in the art world; but Eddie paints a very different picture of the woman's motives. Kirk saves a wealthy, middle-aged art patron, Sabrina Young from being robbed by a mugger. She is so grateful that she gives Kirk lots of expensive gifts and offers to promote his drawings at a big party at her apartment. Kirk belittles the gifts, thinking that people should just do good deeds without expecting any reward. He doesn't believe Eddie's warning that Sabrina is probably just trying to seduce him. There are no guests when Kirk arrives at the party. Sabrina promises Kirk a surprise, and Kirk assumes Eddie was right. He feels cheapened and angrily takes off the tuxedo Sabrina bought him to show that she can't manipulate him into sleeping with her. After Sabrina shows him the surprise, a beautiful frame on his drawing, the upscale guests start arriving. Unfortunately, Kirk is s

Corey needs money to buy his own telephone so he gets a job at the same hospital as Elizabeth. There, Corey meets a grumpy patient who intimidates him. When Kirk visits him, Corey convinces him to help clean the old man's room. To Kirk's horror, they accidentally unplug the man's heart monitor.

Kirk sets Russell straight when the tyke things he got a girl pregnant just by kissing here, but Kirk's unprepared for the parenting rite of passage when Russ asks where babies come from. When Russell asks Kirk where babies come from, Kirk is reluctant to teach him about sex. Nervous, Kirk makes up an outrageous story to explain it, telling him that babies come from rainbows. Later, Russell gets beaten up at school for repeating the story. Finally, Kirk tries to tell Russell the truth, but Russell is no longer interested. Meanwhile, Phoebe tricks Eddie and makes him appear foolish while he's on a date. In order to get revenge, Eddie tries to help Corey annoy Phoebe by entering a better project than Phoebe at a science fair.

Kirk searches for a Christmas miracle when he's fired from his job, his power is cut off because the bill hasn't been paid, and his gifts are stolen. Kirk experiences major disappointments during his first Christmas season in New York City. First, he gets terminated from his job. Then, while he waits for the bus, the packages he bought with his last paycheck get stolen. Kirk takes a job as an elf to earn some extra money. While working, he meets the owner of a comic book company who hires him as a comic book illustrator.

The Hartmans' hopes of beating the Balduccis in a bowling tournament go down the gutter when teammate Sally hurts her back -- but it only gets worse when Elizabeth replaces her. After Sally, an excellent bowler on Kirk's team, hurts her back, Kirk gets Elizabeth to replace her. Unfortunately, he soon realizes that Elizabeth is a terrible bowler. When the team asks Kirk to terminate Elizabeth, Kirk must choose between possibly winning the league championship or being unkind to Elizabeth.

Kirk accidentally intercepts a letter from one of Elizabeth's old beaux saying he'll meet her in New York, but Kirk can't decide whether to tell her the news and risk her anger over the invasion of her privacy. Kirk accidentally opens a letter to Elizabeth and discovers that her former boyfriend, Guy, still loves her. Kirk must decide whether to give her the letter or prevent the relationship from starting again. However, Elizabeth does not want to resume the relationship with Guy. After Kirk tells Elizabeth about how much he cares for her, she agrees to go out on a date with him.

Kirk finally convinces Elizabeth to go on a dinner date with him. Unfortunately, it's on the same night at Russell's school play. Kirk attempts to make each of them happy by trying to be in both places at once. However, Elizabeth is impressed that Kirk cares so much for his siblings. At the end of the evening, Kirk and Elizabeth share their first kiss together.

Phoebe asks Matt, the most attractive boy in her class, to be her date for a school dance. He accepts, but later he claims to have a broken leg and cancels. Kirk convinces Phoebe to go to the dance anyway and takes her there. Unfortunately, Phoebe sees Matt at the dance with another girl--and no broken leg. She gets upset and tells the couple that Kirk is her date. Phoebe's classmates are envious because she's dating an older man. However, when Phoebe sees another boy with whom she wants to dance, Kirk and Phoebe pretend to fight so Kirk can leave. Meanwhile, at home, Corey ignores a promise he made to Kirk and invites a girl to watch TV with him. Unfortunately, her braces get tangled with Corey's new earring when the couple tries to kiss.

When Elizabeth's apartment is damaged by a fire, Kirk insists that she move in with him and the kids while her place is being repaired. Unfortunately, Kirk and she discover just how different they really are. Elizabeth insists on cleaning and organizing everything, while Kirk hates being neat. Just before Kirk's surprise birthday party the two get into a fight, and Elizabeth leaves. Later, they apologize to each other and kiss. Kirk decides that being different may not be completely bad.

Corey & his friends win a night on the town in a chauffeur drivin limo.

Both Russell and Kirk come down with tonsillitis, but it's the older brother who's panicked -- particularly when he learns that Elizabeth will be his surgeon.

Elizabeth's kind invitation to let the Hartmans sit out a heat wave at her parents' beach house does not, of course, work out exactly as planned.