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.

James B. Sikking

as Reverend Foote

Kevin Sussman

as Tiny Shorts Guy

Beau Garrett

as Gloria

Christine Barger

as Psycho Blogger

Lilly McDowell

as Lingerie Salesgirl

Kelly Carlson

as Christie / Wife #6

Craig Susser

as Christie's Lawyer

Corinne Reilly

as Restaurant Hostess

Trip Davis

as Waiter

Valerie Edmond

as Cousin Kelly

Hannah Gordon

as Colin's Mother

Cathleen McCarron

as Cousin Cathy

Eoin McCarthy

as Cousin Ewan

Clive Russell

as Cousin Finlay

Myra McFadyen

as Aunt Minna

Iain Agnew

as Colin's Father

Mary Birdsong

as Sharon at Bridal Shower

Elisabeth Hasselbeck

as Elisabeth Hasselbeck

Grant Thomson

as Huge Scottish Football Player

Te'onna Simone Tye

as Felix's Daughter

Marty Ryan

as Chaise Husband

Veronica Alicino

as Long Island Wife

Sarah Wright

as Sexy Blonde

Jaime Ray Newman

as Ariel / Bakery Date

Ellie Knaus

as Sick Monica

Annalaina Marks

as Barbara / Antiques Date

Edith S. Wolfrey

as Older Lady in Coffee Shop

James Earl Adair

as Guy Selling Alligator Purse

Leah Elias

as Flirting Brunette

Jeff Rudom

as Large Burly Scotsman

Forbes KB

as Man at Highland Games

Murray McArthur

as Driver in Scotland

Rab Affleck

as Sheep Herder

Finlay Welsh

as Ferry Porter

Ron Donachie

as Horse Owner

Jennifer De Minco

as Woman in China Department

Christina Hogue

as Beautiful Girl

Claire M. Fagin

as Older Woman in Boat

Samuel L. Fagin

as Older Man in Boat

Joe Weiland

as Child in Scottish Church

Bella Weiland

as Child in Scottish Church