Carl walks in as Harriette is making a sandwich. She asks him how his day was and tells him he had a great one because he got a stake out at Donut World. Harriette explains to Carl her day was fine until Judy's English teacher, Mrs. Fezlip called her at work. Carl refer to her teacher as Fuzzlip, but his wife says Mrs. Fezlip and reminds him that it's bad enough that everyone at Judy's school calls her by that nickname. Carl reminds her that they've seen her before with her facial hair and needs Electrolosys. Harriette mentions that Judy's on the verge of getting a D in English because she hasn't been doing her book reports in class. So she has to do a book report on Swiss Family Robinson.
Eddie was on a high winning streak after telling Carl about it. He warns his son not to play pool for money, but use it for fun. The next day, he, Urkel and Rodney go to a local billiards hall, The Corner Pocket, after school (ignoring a sign that prohibits underage customers from entering these premises). While there, a nice guy named Boyd Higgins asks him if he'd like to play a little game of eight-ball, for some extra money. Eddie can't refuse, since he seems soooooo very nice. At least that's what he thinks, but Urkel senses something wrong with Higgins because he's seen his kind before. He tries to warn his friend against playing Boyd. but it ends up bing to late for him. Unfortunately, Eddie doesn't know is that he is a professional pool hustler and when he realizes he just got taken. Now all of his money's along with Boyd's nice-guy demeanor are gone. Now, he has demanded that Eddie return for a high-stakes match, and if he doesn't bring the $250 he owes him, there'll be serious trouble for his family and friends.
Rather than go to his folks for help, Eddie tries to settle the matter by himself by heading down to Rachel's Place where Steve works with Laura and appealing to him for help. He refuses at first because he wants to buy a telescope, but Rodney tells him there's no time for it. Urkel eventually agrees to give him the $250, under two conditions: one, he accompanies them to the Corner Pocket. Both Eddie and Rodney agree with that. Two, he has to be his best friend for a week. When Eddie tries to resist, he remnds him that dead men don't bargain. The younger Winslow agrees to the terms and before Steve was about to leave with them. Rachel shows up to remind him that his shift starts soon and Laura's shift will end. Unfortunately, Urkel lets it slip to her that Eddie is in trouble with Boyd and his bodyguards at the Corner Pocket and if he doesn't pay his dues, they would severely beat them up.
At the Winslow Kitchen, Judy complains to Harriette how boring the book is because it's thick and long. That is until, she decides to do a little reverse psychology by telling her that she thought about how bored she was with reading about a family who got stranded on an island, built a tree house and warded off a bunch of pirates. Judy thinks it's cool and ask her about it. Harriette reveals that it was indeed Swiss Family Robinson, but reminds her that she isn't interested. However, Judy disagrees and takes the book from her to read it. Carl comes down the stairs and asks Harriette about the reading. She mentions that it's coming along.
Accompanied by Rodney and Urkel, Eddie returns to The Corner Pocket pool hall and gives Boyd the $250. Steve takes the money from him and challenges him for a double or nothing game. Eddie insists he gives Higgins the money right now because he and Rodney wants to leave. Urkel agrees if Boyd is a chicken to accept his challenge. The pool denizens turns their attention towards him as Higgins demands for an answer for the insult. Steve insists he gives it a shot and Higgins agrees to an 8-ball game. Boyd learns how good Urkel really is at the game and was three balls away from winning all of his friend's money back. That is until Higgins' two bodyguards breaks the nerd's glasses. When Urkel starts to resist, the thugs under Boyd's orders, escort the hapless 80-pound weakling out and take him away.
That is until, his bodyguards are forced back in by an imposing Carl accompanied by an equally imposing Estelle "Mother" Winslow. Eddie asks them how they knew where he was. Carl tells him that Urkel told Rachel about what's going on here. Steve gives them the insight about what happened with $500 on the line and his glasses are broken. After a few seconds of summary, he tells the pool hustler, Higgins, that he and Mother Winslow are going to fill in for Urkel. When Boyd tries to complain about it, Carl adamantly tells him that he can look around hard enough to see a couple of laws being broken inside The Corner Pocket. He gives Higgins a choice: either allow him to fill in for Steve or he'll arrest him and escort him to Cook County Jail. Boyd agrees to let him fill in on the grounds that no one will owe anything. Carl and Mother Winslow then take the pool hall bullies back to school and win back the money Eddie lost.
At the Winslow home, Eddie gets a stern lecture from Carl about not heeding his and Urkel's warning against playing pool for gambling. The younger Winslow admitted he thought he could beat Boyd, but he was proven wrong. Eddie revealed if Steve hadn't told Rachel about what happened him, Carl and Mother Winslow wouldn't had bailed him out and he would've been pounded by Boyd and his bodyguards. He opts for an early retirement from pool, but Carl reminds him that he shouldn't play for money. He even mentions that no matter how good he is, there's always someone better than him. Eddie agrees, but he reveals no one tops his father. He even admitted that to there the worst part about him being in the mess he was in when he was in trouble with Boyd Higgins. In order to get the reluctant, Steve to help bail him out by loaning him the money, he had to be his best friend for a week.
Eddie hopes he could luck out and Urkel would forget about the whole thing. Unfortunately, Steve didn't forget and Carl leaves as he mentions their plans. It isn't long until Eddie's crying about it as he reads out the time and the places they'll be going to during their week tenure as best friends.