
Tom and Hannah have been platonic friends for 10 years. He's a serial dater, while she wants marriage but hasn't found Mr. Right. Just as Tom is starting to think that he is relationship material after all, Hannah gets engaged. When she asks Tom to be her 'maid' of honor, he reluctantly agrees just so he can attempt to stop the wedding and woo her.

Patrick Dempsey
Tom

Michelle Monaghan
Hannah

Kevin McKidd
Colin

Kadeem Hardison
Felix

Chris Messina
Dennis

Richmond Arquette
Gary

Busy Philipps
Melissa

Whitney Cummings
Stephanie

Emily Nelson
Hilary

Kathleen Quinlan
Joan
Selma Stern
Grandma Pearl

Sydney Pollack
Thomas Sr.

Burning Blue
Burning Blue

Chindia
Chindia

Breaking the Waves
Breaking the Waves

The Good German
The Good German

Before Sunset
Before Sunset

Eternal Sunshine of the Spotless Mind
Eternal Sunshine of the Spotless Mind

Young Adam
Young Adam

Breakfast at Tiffany's
Breakfast at Tiffany's

Pretty Woman
Pretty Woman

Bapi Bari Jaa
Bapi Bari Jaa

Bad Newz
Bad Newz

Scotch
Scotch