The narrator says twice in the opening that Rip is good natured and that this earns him "universal popularity." He is easy going, he lives in the moment, and he likes people. He is always ready to stop and help a child or a neighboring woman. It is his own family he neglects as he goes about in his happy-go-lucky way, unable to earn a decent living. Significantly he likes to spend long, sleepy afternoons at the inn sitting aimlessly with other men outside under the portrait of George III. In many ways he represents the friendly and affable but unfocused and exploitable pre-Revolutionary American, content to go with flow. He will be amazed after he wakes from his 20 years of being asleep to find out how engaged, energized, and purposeful the new United States has made people.

Rip Van Winkle was universally loved by everyone in the village with the exception of his wife. The narrator notes, for example, that "The children of the village, too, would shout with joy whenever he approached." At the same time Rip was "a great favorite among all the good wives of the village." In fact, Rip was so universally liked that even the dogs of the village loved him and not a single one would bark at him. The one exception, of course, was Rip Van Winkle's wife who found him to be a lazy, good for nothing, disappointment. Whenever Rip came home, his wife would tear into him about his myriad of failings. As a result, Rip avoided being at home or on his farm and spent his time wandering the woods to escape from his wife. The irony of course is that everyone loved Rip except for his wife who should have been his closest companion.