Ever since the idea of an extra day every four years was implemented as a corrective measure for the calendar, it has been filled with traditions and superstitions. One of these is the (shocking!) idea that a woman may propose to a man on February 29th (or anytime during a Leap Month or even the whole Leap Year), instead of the other way around.
The origin of this tradition is murky. There is an Irish legend that states that St. Brigid asked St. Patrick to allow women to propose to men. He agreed that this would be okay on Leap Year. This was supposed to keep a balance between men and women in the same way that a Leap Year keeps a balance in the calendar.
The right of a woman to propose is also said to derive from early English law, which did not recognize the Leap Day as a real day. Because it was not a “real” day, many traditions were also ignored.
Still another legend has it that in 1288, Scotland made it legal for women to propose to men not only on Leap Day, but anytime in a Leap Year. If the man said no, then he was supposed to buy her presents ranging from dresses to gloves.
Whatever the origin, the legend naturally led to some fun. Leap Year parties and dances in which the women could ask the men out flourished. It was also an opportunity for humorists to poke fun at single women and the power they suddenly held in a proposal.