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David Letterman was suggesting it as a tongue-in-cheek money-saving tip for Valentine’s Day. By breaking up briefly before the holiday and getting back together after, one could avoid having to buy gifts, flowers, chocolates or take their partner out for a fancy Valentine’s Day dinner.
Of course, most partners would not appreciate such a scheme and it was likely meant as a joke highlighting ways to save money by forgoing traditional Valentine’s Day celebrations and gestures of affection.