Why should gender and sexuality matter if love is possible? Contrary to the sarcastic disembodied voice in his head, Brooke Tristan Flynn is not your average community college student. He is an unparalleled fool for love. When he is re-introduced to Lorelei, his childhood love, who is without a doubt, a lesbian, Tristan must summon all his strength as a man to become a woman. By using healthy amounts of cover-up, concealing wardrobe choices, and plastic boobs Tristan begins his satirical hero’s journey to prove that love supersedes appearance. Tristan is aided in this charade by his friends. Patty, who becomes so inspired by Tristan’s romantic notions, she makes her own ill-advised relationship decisions. Matthew, a gay man, who harbors his own secret crush, and Charlotte, a semi-demonic hairdresser endowed with the gifts of makeover and temptation. Tristan must overcome the doubts within himself, as well as the society at large, to be worthy of the otherwise impossible---true love.