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| Patrick Dempsey | Tom |
| Michelle Monaghan | Hannah |
| Kevin McKidd | Colin |
| Kathleen Quinlan | Joan |
| Sydney Pollack | Thomas Sr. |
| Kadeem Hardison | Felix |
| Chris Messina | Dennis |
| Richmond Arquette | Gary |
| Busy Philipps | Melissa |
| Whitney Cummings | Stephanie |
| Emily Nelson | Hilary |
| Selma Stern | Grandma |
| James B. Sikking | Rev. Foote |
| Kevin Sussman | Tiny Shorts Guy |
| Beau Garrett | Gloria |
Always shy of commitment, Tom lives as a serial dater. Hannah, his best friend, has wanted to marry and now has found Mr. Right -- just as Tom realizes he really loves Hannah. When she asks him to be in her bridal party, Tom seizes the opportunity to prevent the nuptials and woo her himself.
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