Rip is popular with the children of the village because he “helps at their sports, makes their playthings, teaches them to fly kites and shoot marbles, and tells them long stories of ghosts, witches, and Indians.” The children like to follow him around during his strolls in the village. They “hang on his skirts” and play all kinds of jokes at him. In other words, the children consider Rip a fun playmate and companion. This could be because Rip is a generally happy person with a sunny disposition, often willing to assist others with their tasks. Even the older people in the village like him.

The story states that Rip’s only weakness is his inability to engage in any form of “profitable labor,” especially those that can improve the lot of his family. As such, his children are “ragged and wild” and his wife, a querulous woman, constantly nags him about his “idleness and carelessness.” Her nagging becomes so bad over time that Rip really does not know what to do with himself. Thus, the twenty-year sleep he has after drinking off the flagon of the strange men up the Catskill Mountains kind of takes away the burden of his wife off him. When he comes back from the mountains, twenty years after he left the village, he finds that his wife is already dead. He is taken in by his daughter, who is already married and has a farm of her own.