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
as Tom

Michelle Monaghan
as Hannah

Kevin McKidd
as Colin

Kadeem Hardison
as Felix

Chris Messina
as Dennis

Richmond Arquette
as Gary

Busy Philipps
as Melissa

Whitney Cummings
as Stephanie

Emily Nelson
as Hilary

Kathleen Quinlan
as Joan