

It takes a real man to become a maid of honor.
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.

Just a Question of Love
7.3 · 2000 · Movie

The Royal We
6.4 · 2025 · Movie

What Women Want
6.5 · 2000 · Movie

This Sweet Sickness
6.5 · 1977 · Movie

Under Capricorn
6 · 1949 · Movie

The Knight
· 2025 · Movie

The Private Lives of Pippa Lee
5.9 · 2009 · Movie

Indecent Proposal
6.4 · 1993 · Movie

Veer-Zaara
7.5 · 2004 · Movie

Where Love Lives
· 2025 · Movie

Knocked Up
6.3 · 2007 · Movie

Keeping the Faith
6.1 · 2000 · Movie