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
Selma Stern
as Grandma Pearl
Sydney Pollack
as Thomas Sr.
