2000-03-17 • 1h 53min
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".

Chasing Amy

Swingers

The War of the Roses

Pushing Tin

Sliding Doors

The Wedding Singer

High Road

Funny Farm

Bobby

Polyester

City Hall

Wajib

2001 Maniacs

What a Crush

Burnt Money

Girlfriend's Day

Anatomy

Hateship Loveship

Evelyn

In the Bedroom