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How far out should couples order their wedding cake? “That all depends on the difficulty of the design, Mary Winslow of Sinful Wedding Confections tells The Wedding 101 Show host David Rothstein. “The season you want to get married in is also a key factor. So a general range for the height of a wedding season—between Memorial Day and Labor Day—would be five to six months. But if you’re getting married in February, you could easily book your baker in January, because that’s such a slow season.”