After his long-time girlfriend dumps him, a thirty-year-old record store owner seeks to understand why he is unlucky in love while recounting his "top five breakups of all time".
John Cusack
Rob Gordon
Iben Hjejle
Laura
Todd Louiso
Dick
Jack Black
Barry Judd
Lisa Bonet
Marie DeSalle
Catherine Zeta-Jones
Charlie Nicholson
Joan Cusack
Liz
Tim Robbins
Ian Raymond
