Nobody’s Perfect (1989)

Steve is a college freshman who plays tennis for the school. But he falls desperately in love with Shelly, also a tennis player. It’s all downhill from there. Steve can’t eat, he can’t sleep, his grades drop, and he gets kicked off the tennis team. What can he do? Well, his resourceful friend suggest turning Steve into a woman in order to get him close to Shelly who doesn’t know he is alive.