Meet Chris Waitt, a hapless thirty-something filmmaker, unsuccessful musician and complete failure of a boyfriend. But when Chris' latest girlfriend dumps him, he decides to create an honest chronicle of his disastrous romantic history. Now armed with a camera, boom mike and some help from his mom, Chris is tracking down and interviewing all of his old girlfriends in hopes of finding out what went wrong...or maybe even hooking up again. Along the way, he'll learn some brutally hilarious truths about relationships, responsibility and his own sexual dysfunction, including punishment by a dominatrix and an overdose of Viagra. It's an uncompromisingly funny journey of self-discovery - and a sometimes poignant ex-love story - about one man's mission to re-open any emotional wound just to get a little closure.