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Lucky is annoyed with all of his brothers and sisters because he can't watch TV or eat without them getting in his way. When he confronts his parents on this, they tell him that whilst having a big family can be tough, he'll never be lonely and they all love him. Lucky, however, continues to protest on how he wants his own bed, food, and TV, before Perdita comes up the idea for him to stay at Aunt Coco and Uncle Beamer Vandercream's, a sophisticated, glamorous aristocratic Dalmatian couple. Lucky instantly agrees, much to Cadpig, Rolly, and Spot's shock.
Lucky sets off to the Vandercreams on the back of a grocer van and soon arrives at their mansion. Lucky meets his aunt and uncle along with their butler, Gieldgud. During dinner, the Dalmatians are served kibble cocktails, to which Lucky chows down. Lucky apologizes for this after seeing Coco and Beamer's shock; however, they are more shocked to hear they ate out of a trough and hope they aren't too late to get his "farm damage." Lucky asks if they are finished in dinner; however, he learns that was only his first course. Lucky is then presented with a steak, and he is overjoyed.
Lucky soon gets a large room all to himself that includes small plush animals, dolls, and a "Chase-O'-Matic" (a treadmill with a screen so he can chase anything he wants).
Meanwhile back on the Dearly Farm, the other pups begin to miss Lucky and wonder if he misses them, so they have Pongo and Perdita send a message via the "Barking Chain" to see how he's doing. He responds by saying he's having a great time. Perdita is surprised by this as she expected him to be ready to come home by that time, Pongo assures her to give Lucky more time. Cadpig, Rolly, and Spot have concern that Lucky has gone material and if he'll ever come back.
The next day, Lucky is on the "Chase-O'-Matic" before Coco and Beamer come to take him for a walk, they also tell him they arranged a play date at the dog park (they're obviously dogs anyway). On the play date, Lucky meets two other high class dogs called Sha-Sha and Clyde. Neither of them want to dig holes nor chase squirrels, feeling it is beneath their dignity, however when they suggest they play disk toss, Lucky discovers that rather than catching the Frisbee their humans throw, the human does all the work. Lucky then realizes that all the high class dogs in the park get their humans to do any dog-like work for them (e.g. pull them along on a skateboard or bury their bones).
Lucky soon gets homesick and is reminded of Rolly at dinner, it isn't made any better considering the second course is chicken. Later, Lucky turns on Thunderbolt, yet he doesn't find it as fun to watch by himself, so he asks Coco and Beamer if they like to watch, but they find it too unsophisticated for them. Lucky whimpers and howls into the night, which gets picked up by the "Barking Chain."
The next day, Lucky is awoken by the voices of the other pups and much to his delight, he sees the Dearlys have come to pick him up. The other pups dog pile on top of Lucky, with him happy to see them all.