In the late 1990s, Japan and South Korea concluded their first bilateral free trade agreements (FTAs) in completely opposite sequences despite similar domestic pressures. Japan concluded an “easier” FTA with Singapore first and then concluded a more “difficult” FTA with Mexico. South Korea concluded a more difficult FTA first with Chile and then moved on to negotiate with Singapore. In this article, I analyze these cases and review the literature on bargaining and two‐level games to develop a model of how these differences in sequence account in part for the relative differences in each country’s bargaining strength in their more difficult negotiations. The preexistence of the Singapore FTA eased domestic pressures to reap the benefits of entry into the bilateral FTA game. Thus, Japan could approach the more difficult FTA negotiation knowing that a “no‐agreement” outcome would not fundamentally increase domestic pressure to get into the free trade “game.” This alternative to no agreement put the Japanese in a stronger international bargaining position. South Korea negotiated its harder case knowing that the relative domestic pressure to get in the FTA game would increase without an agreement. This relatively worse bargaining position created a context in which South Korea conceded more internationally at the expense of higher side payments domestically.