Back in the Sixties while Motown hits filled the airwaves, naive Jill Novak acknowledged her knack for choosing losers when boring Husband Number One vanished, leaving her to support their two-year-old. Afflicted with planning deficit disorder, the perpetual daydreamer soon morphs from small town Jill to sophisticated big city Cherie, but a new name does not a better future bring. In 1969 Houston, Cherie encounters a rogue's gallery of characters unlike those from her small Texas hometown; a drop-dead gorgeous transsexual, a snarling wannabe Mafia hit-man, a hairy cop who incorporates fondling girls into his job, and a ditzo neighbor whose desire for friendship borders on stalking. But it is two distinctly different men-a middle-age gregarious gambler and a twenty-something gruff intellectual-who jump on board her turbulent thirty-year roller coaster ride and journey with her into the 21st Century and womanhood."