Man Is a Woman (1998)

It's an experience that every man ought to have at least once in his life... to be for just a moment a woman in the arms of a man...

Simon Eskenazy is a gay Parisian clarinet player who lives his single life to the fullest. One day, he receives a very tempting offer from his homophobic uncle, looking to continue the family legacy – if he gets married and has a child, he will receive ten million francs and inherit his uncle's luxurious mansion. After meeting Rosalie Baumann at his cousin David's wedding, and with some convincing on his mother's part, Simon sees an opportunity to fulfill his uncle's wishes and the pair go ahead and get married, but not before traveling to New York to meet Rosalie's Orthodox Jewish family. As Simon tries to develop real feelings for Rosalie, he struggles with his feelings for his newlywed cousin David.