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In the small, rural town of Sandusky, Ohio, two goth kids are each other's best friends, sharing their experiences of being the town outsiders. Teenage photography enthusiast Clive (Kett Turton) is on his way towards coming fully out of the closet, and Gypsy (Sara Rue) is an overweight 25-year-old girl with a love of Stevie Nicks music and a low-pay job at the photo hut in the parking lot of the local mall. When the duo hears about a "Night of a Thousand Stevies" karaoke show in New York City, they decide to make a road trip of it as a way to escape the drudgery of small-town Ohio in the heady nightlife of NYC.
Follows a guy who has it all, success, women, charm. One day he loses it and, in his fall, starts going through his book of exes to find out who he really is.