“The Gypsy Smiled” is the story of Lucretia “Lucy” a 19-year-old gothic singer in the early ’90s trying to make it on her own. She’s in an original band and juggles two jobs. When a younger guy, Dionysis, a.k.a highschooler Scot, befriends Lucy she ignores her true feelings. Aside from their fake names and being a part of the gothic subculture, they are also huge “oldies” music fans.
Scot wants to take the relationship to the next level, but Lucretia would rather live in her fantasy world, dreaming about her favorite “oldies” musician Lou Christie; and her band making it. However, Lucy’s make-believe world is a far cry from reality. That’s when her good friend, a psychic who goes by “Gypsy,” forces her to slow down and sends her to an all-expense paid new age spa in the country for some relaxation and reflection. What happens next? Only Gypsy knows!