The audience follows the life of a young man named Neil who has terrible luck in love. Unbeknownst to Neil, much of his disastrous bad fortune is due to his dead, overbearing mother, Elaine, meddling in his love life. Drama unfolds as Neil seeks to break his unlucky dating streak, while simultaneously helping his father find love again. An endearingly nosy upstairs neighbor, Millie, and her smooth-talking late husband, Fonzie, are among the quirky characters who interfere in Neil's romantic escapades as the story progresses.