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