Rip's sleep's real meaning is that he is escaping from his family and his responsibilities. Irving, the author of the story, had Rip draw in to sleep in the first place, so his character could have an adventure when he woke up, not just so he could escape the present. It's important to see both points because Rip going into the spiritual woods means both escape and adventure. The point that Irving was making was that slowness will cause you to miss out on the things of the future. This story is like showing us what would happen if we could escape our responsibilities and come back at a convenient time. The fact that Rip's wife had always nagged on him didn't make him sorry that he slept for as long as he did. He was actually relieved because he escaped the snatch that his wife had on him. It seemed that she took away a part of his man-hood by always telling him what to do and what not to do. Rip then returned back to the town square and realized what had happened. Not too many people believed his story but reality struck and people started believing him. He was no longer looked at as a lazy irresponsible man, but as a hero.
During the Romantic Period of American Literature it was believed that imagination is greater than logic and that imagination is the greater solution to finding truth and beauty, what most authors valued. Romantic writers also believed that cities led to corruption; therefore nature is a safe place to become more spiritual. This is why Rip Van Winkle schemes into the forest with his dog to escape the attack of his wife. Sleeping for 20 years is where the "imagination is greater than logic" part comes into play. The moral of the story, however, is to have your priorities in order. Rip helped neighbors whenever possible, yet was unwilling towards his family. Of course sleeping for 20 years isn't reasonable for us. Whether Irving is romantic or not, the point is to display to every reader throughout time that we cannot sleep through a revolution, or shrink our responsibilities.
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