Nemo's niece, Angelina, takes employment at Nemo's as a waitress at Nemo's. When Angelina catches Ray's eye, he has a lot of explaining to do to his wife, Debra especially when Angelina calls him at home. Ray accidentally leaves his wallet at Nemo's, and Angelina calls him at home to let him know she found it. But, because he feels guilty about his innocent attraction, Ray denies ever knowing her. When the situation is blown out of proportion by the Barone family, Debra decides to visit Nemo's to see what all the fuss is about.

Ray gets tired of being treated like a kid at his father's poker game, so he ignores his father's advice and ends up losing all his money. Debra wants Ray to act like a mature adult and ask Frank for his money back, but Ray is too stubborn. Meanwhile, it turns out that Frank was only trying to teach Ray a lesson - that you can always go to your father and he'll make everything okay.

When Ray's "free" time goes to coaching his basketball team in preparation for the Pizza League championships, he is reminded by Debra that their kids are growing up fast and he's missing precious time with them. When Robert is forced out as captain of Nemo's basketball team, Ray gets the title and the opportunity to lead his team to victory. Meanwhile, Frank and Marie are upset with Ray for de-throning Robert as captain, and feeling guilty Ray begs Robert to re-join the team.

When Raymond takes over the family checkbook to prove to Debra how "easy it can be" to balance it, he discovers he is no accountant. After he quickly runs out of money and starts bouncing checks, he tries to hide the truth from Debra and winds up entangled in a mess of lies, two fake checkbooks and a large loan from his brother.

Raymond decides to spend a shift accompanying his brother Robert, a policeman. Initially, spending a shift in the back of Robert's patrol car bores Raymond and he wonders why he even bothered putting on the bullet-proof vest. But his boredom quickly turns to terror during a chance visit to Nemo's restaurant that puts them in the middle of the hold-up. When Robert saves the day by throwing a hot pizza in the burglar's face, Raymond sees for the very first time how courageous his brother really is.

After Debra suggests that she might be more consistently romantic if she weren’t in charge of the birth control, Ray decides to make the drastic move of “cutting the wires.” But after a discussion with Robert, and other top “medical experts” he chickens out, but does muster enough bravery to go to the drugstore and buy “the stuff.” He even goes crazy and splurges on “the rainbow pack” but the plan for Halloween romance goes awry when Grandpa distributes the “chocolate coins in brightly colored wrappers” that he found to the remaining trick-or-treaters in the neighborhood.