Jon just makes a flight to New York City, and he is relieved that he is taking a vacation without Garfield (in actuality, Garfield is hiding inside one of his bags). Jon then notices that an attractive woman (Roselyn) is sitting next to him, and because Jon is a tourist in New York, she offers to show him around the city. (A mysterious man sitting behind them monitors their conversation).
Just before the date, Jon is in his hotel room, and he opens his bag and Garfield jumps out. He then discovers that Garfield replaced all his toiletries with canned lasagna (and a can opener). He then orders Garfield to stay in the hotel while he is on his date. Jon then meets Roselyn, who takes him to an Italian restaurant, and Garfield sneaks behind them.
While at the restaurant, Garfield overhears the mysterious man on the phone revealing that Roselyn is a pickpocket. Garfield then sabotages Jon and Roselyn’s dinner and then threatens Roselyn. Jon takes her, runs out of the restaurant and hops a cab. They wind up at an art museum, and Garfield is hiding inside one of the pictures. He jumps out when he sees Roselyn reaching into Jon’s coat (presumably for his wallet). Jon and Roselyn then try to escape at the top of a skyscraper; then they find Garfield at a public museum. Jon excuses Roselyn so that he can settle with Garfield, and right before she leaves, she succeeds in taking his wallet.
Jon searches for his wallet in order to give Garfield money for a cab, and then Garfield convinces him that Roselyn took the wallet. They run down the stairs and find the Roselyn with the mysterious man, who turns out to be a detective. He returns Jon’s wallet to him and then leaves with Roselyn; then Jon apologizes to Garfield, whose repayment is being taken back to the Italian restaurant. After the dinner plates pile up, Jon remarks that it would have been cheaper to let Roselyn keep the wallet.