Freshly dumped and deeply despondent over what seems to be an endless string of disastrous relationships, lovelorn filmmaker Chris Waitt attempts to root out the source of his romantic woes by tracking down each of his ex-girlfriends and asking them point blank about his shortcomings as a boyfriend. The answers Waitt receives are frequently as pointed as his questions, providing unguarded insight into the psyche of a self-absorbed, semi-delusional Lothario who rarely managed to arrive for a date on time much less follow through on his pillow-talk promises. Later taken to task by his own mother, the long-suffering relationship bungler eventually turns to therapy, acupuncture, and even Viagra in hopes of learning the secrets to loving like a true grown-up.