Discovering her passion for costume design rather late in life, Atlanta resident Jennifer O'Donnell was on the cusp of realizing her dream. However, this dream was deferred when she got married to Tim, a long lost acquaintance who had been widowed while still trying to take care of his son. Selflessly, Jennifer put her career aspirations on hold to care for a grieving child to whom she was now an instant mom. Now a few years later with a more stable family situation, Jennifer is ready to resume her career and pick up where she left off. Kurt whisks Jennifer to New York City where she studies under the tutelage of Emmy Award-winning costume designer Donna Zakowska. On offer is a potential place on the costume design team of the new Broadway show "Kinky Boots." While husband Tim is supportive of Jennifer's dream, he is also cautious. New York is a world away, and what would Jennifer's absence or their relocation to the Empire State mean for their family, especially their young son?