Rip Van Winkle's overriding character flaw, at least according to Dame Van Winkle, is his chronic idleness. Rip is uninterested in farmwork or his domestic duties, and this contributes to his wife nagging him constantly. She has to worry about their “ragged” children and failing farm while Rip hunts in the Catskills, drinks at the inn, tells stories to the local children, or volunteers for odd jobs around the village, which inevitably causes Dame Van Winkle to feel a considerable amount of resentment toward Rip.

Rip's supposed character flaw is chiefly responsible for his lack of success in life. His farm is not doing well; in fact, it is “the worst-conditioned farm” in the village. Rip believes that attempting to improve his land is a waste of time, as everything seems to go wrong with it in spite of his best intentions. On the face of it, it seems that Rip is just the victim of bad luck; however, one gets the impression that Rip's lack of good luck as a farmer is directly related to his aversion to farming.

Interestingly, Rip doesn’t demonstrate this same quality of idleness as a neighbor or community member; he is known around the village for always lending a helping hand and for his competence with fence-building, corn-husking, and other tasks. “In a word,” the narrator says, “Rip was ready to attend to anybody’s business but his own.” Even left to his own devices, Rip is capable of spending long hours fishing and hunting without complaint. His disinterest in farmwork, however—combined with his easygoing nature and his status as a regular at the village inn—leads Dame Van Winkle to accuse Rip of indulging in “habits of idleness.”

Rip's twenty-year slumber can be seen as the natural extension of his sleepy personality, as well as an unintended way to permanently avoid Dame Van Winkle’s demands. When he wakes up from his enchanted sleep and reintegrates himself into the village, there are no further demands upon him at all, and Rip is free to live out the rest of his days in tranquility at the inn.

What character weakness did Rip Van Winkle have?

Rip Van Winkle is a happy-go-lucky soul. Children love him, and he is always willing to help out the wives on neighboring farms with a task here or a task there. His character weakness, however, is a complete lack of drive or ambition. He lets his wife, who is understandably angry and frustrated, run their falling apart farm while his children are neglected and run wild. Rip doesn't take responsibility for bettering himself or caring for his own family.

Rip would rather be sitting in front of the inn, talking about old news events, or out in the woods hunting and fishing. He is passive and apathetic.

He represents the colonial character, the kind of person who would rather be the subject of a monarch than a citizen in a democracy. This becomes clear after he wakes up from sleeping for twenty years. In this time, the American colonies have broken away from England and established their own nation. The vigorous, engaged citizens of the new democracy are a far cry from Rip, who is considered a relic of a bygone age.