Let It Snow

Let It Snow is a 1999 American romantic comedy film directed by Adam Marcus and written and produced by his brother, Kipp Marcus, who also stars. Additional cast members include Alice Dylan, Bernadette Peters, Larry Pine, Henry Simmons, Judith Malina, and Miriam Shor. The story involves a young man who finds love during "snow days" time off from high school, but spends years finding his true self. He is haunted by a family curse—as told to him by his grandmother—that the men in the family are doomed.

Synopsis from Wikipedia, CC BY-SA 4.0. Everything below written here.