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".

• Touchstone Pictures
• Working Title Films
• John Cusack
• Iben Hjejle
• Todd Louiso
• Jack Black
• Lisa Bonet
• Catherine Zeta-Jones
• Joan Cusack
• Tim Robbins