Ray Barone is a successful sportswriter living on Long Island with his wife Debra, daughter Ally, and twin sons, Geoffrey and Michael. Ray's meddling parents, Frank and Marie, and brother, Robert, live directly across the street.
When Debra comes down with the flu and is bedridden, so now the inexperienced Raymond must take care of her and the three kids.
Ray can't face the fact that everybody thinks that his brother Robert is "classically handsome," while they consider him "adorable like a hamster."
Debra, already annoyed at getting stuck driving the old car Ray bought from his parents, really gets upset when she discovers that it was his old "make-out-mobile."
Ray finds out that the diamond on Debra's engagement ring is a fake, so he steals it from her to get it changed, only to find out after that she already had it exchanged it with her grandma's $15,000 diamond.
When Ray and his family play a game of Scruples after their cable goes out, they find themselves arguing about honesty. To make matters worse, when Ray complains to the cable company about the disruption in service, he is informed that he has an illegal hookup.
When Debra tries to change Ray's pessimistic attitude about winning the Sports Writer of the Year Award, he agrees to change his ways and become more positive, but he soon has to suffer the downside of being the only optimist in his family.
