This article considers the unconventional and chimerical custom of women proposing to men during a leap year. Capturing the imagination of Americans from 1904 into the 1960s, shame and ridicule made it difficult for women to take advantage of the opportunity to propose to men. Critics held that women who asked men to marry them were desperate, aggressive, and unfeminine. Considering postcards, advertisements, and newspaper columns, this article concludes that the leap year tradition promised real power for courting women but ultimately delivered false empowerment and reinforced traditional courtship practices.