A Date with Miss Fortune is a romantic comedy about the fantasy of love at first sight — and what happens when that fantasy simultaneously crashes into reality. Jack (Ryan Scott) is a struggling writer whose hopeful ideals have been squashed by rejection and loneliness. One day, when a superstitious Portuguese beauty named Maria (Jeannette Sousa) rescues him from a near-accident, his life and luck suddenly begin to turn around. During their accidental "first date," Jack and Maria are taken through a magical series of flash-forwards to their future life together.