One of the main conflicts in "Rip Van Winkle" is the tension in the marriage between Rip and Dame Van Winkle. The two characters have such different personalities, and their lack of compatibility is so blatant, that one might wonder how they ever got married in the first place.

Their marriage, such as it is, is riddled with conflict based on their diametrically opposite personalities and on their radically different outlooks on life. Dame Van Winkle is described as a "termagant" and a "virago," a woman with a sharp tongue and fiery temper. Rip Van Winkle, in contrast, is described as a "simple, good-natured" soul who just wants a quiet life.

Much to his wife's annoyance, Rip does little or no work around the house or farm—preferring to fish, hunt, do odd jobs around the village, or spend time at the inn instead—and the little he does do is invariably ineffective. It is not surprising, then, that Dame Van Winkle is constantly nagging Rip about his failings as a farmer and a husband.

It is in order to avoid his wife's nagging that Rip regularly takes to the Catskill Mountains to hunt and to enjoy some much-needed peace and solitude. It is during one such jaunt that he ends up falling into an enchanted sleep. When Rip wakes up from that sleep twenty years later, he finds out that his wife has passed away. In that sense, then, one could say that it took Rip's lengthy slumber to resolve the conflict between him and his wife.