What Boys Like (2003)

While traveling to be the groomsmen in the wedding of their friend Scott, the wolf Dewey proposes two bets to his monogamist friend Jay: if he had sex along the weekend he would give his valuable convertible car to Jay; and if Jay did not score any woman in the same period, he would date Jay's sister. They arrive in a huge property with their loser friend Phil, and the trio is introduced to the bridesmaids. When Jay meets the fiancée Reese, he realizes that she is his former sweetheart and passion. Along the weekend, the bets and the love of Jay for Reese gets the guests into very complicated situations.