Follow Caskey, a 20-something gay actor from the Midwest as he navigates New York City, his fledgling career and his complicated love life. Season one finds Caskey with a big national advertising job with some disastrous results. Meanwhile, he begins dating a set-up from his friend, Kelly, who's carrying a particularly unique bit of baggage. Join Caskey as he deals with a national PR scandal and a psychotic ex along side his fashionista cohort Eva and his aggressive agent, Susan.