The Gypsy Years (2000)

The story of a group of friends immediately post college, living in their working class hometown, just outside of Boston. A town on the edge of hip, and this side of trendy, but full of working class people with meaningful stories, albeit with complicated family dramas and financial duress. Katherine "Mossy" Moss is the one person out of her group of high school friends who has spent the last four years in an elite out of state academic institution. Upon graduation and breaking up with her college boyfriend, Mossy returns home to the familiar complexities of life in a small town, moving back in with her single mother and adolescent brother. While trying to infuse her college experience into the world she grew up in, Mossy struggles to come back into the terrain of her old friends who have stayed behind. Mossy pines for the moment when she can be financially free to do as she pleases with her own professional career and to go into the "real world" with confidence, but in the meantime must learn to find good in the place she remembers only hating. It is that time in her life where Mossy wavers between youthful angst and grown up goals, not really understanding either, or how they are to co-exist in her life as she plunders through regaining friendships and family, and reclaiming true love with an old heartbreaker.