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Wheel of Fortune and Fantasy is an anthology film consisting of three parts that explore love, desire, and reality in Tokyo. The film depicts various encounters and relationships, including a love triangle, a first love, and a honey trap. It delves into the themes of erotic literature, chance encounters, and the blurred lines between fantasy and reality.

Hard-hearted New York novelist Dru Cassadine...known for her holiday romance stories (even though she is antilove and anti-Christmas)...is desperate to get her mojo back after a string of flops (and a not-so-subtle threat by her publisher that he'll drop her if she has another failure). She decides that a change of scenery might get her creative juices flowing and heads south for the winter, landing in a place known as Harbor Pointe. She doesn't quite get what she came for. She gets much more.