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.

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.

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