We study strategic issues in the Gale-Shapley stable marriage model. In the first part of the paper, we derive the optimal cheating strategy and show that it is not always possible for a woman to recover her women-optimal stable partner from the men-optimal stable matching mechanism when she can only cheat by permuting her preferences. In fact, we show, using simulation, that the chances that a woman can benefit from cheating are slim. In the second part of the paper, we consider a two-sided matching market found in Singapore. We study the matching mechanism used by the Ministry of Education (MOE) in the placement of primary six students in secondary schools, and discuss why the current method has limited success in accommodating the preferences of the students, and the specific needs of the schools (in terms of the "mix" of admitted students). Using insights from the first part of the paper, we show that stable matching mechanisms are more appropriate in this matching market and explain why the strategic behavior of the students need not be a major concern.Stable Marriage, Strategic Issues, Gale-Shapley Algorithm, Student Posting Exercise

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