Hilary Duff as Holly Hamilton

Heather Locklear as Jean Hamilton

Chris Noth as Ben Cooper

Mike O'Malley as Lenny Horton

Ben Feldman as Adam Forrest

Vanessa Lengies as Amy Pearl

Caroline Rhea as Gloria

Kym Whitley as Dolores

Aria Wallace as Zoe Hamilton

Michelle Nolden as Amber

Carson Kressley as Lance

Curtis Fletcher as Wedding Usher

Maggie Castle as Wichita Girl

James McGowan as Jean's Suitor

Gerry Mendicino as Market Co-Worker

Philip Akin as English Teacher

Jeff Lumby as Dr. Fitch

Monique Mojica as Principal Campbell

Marvin Kaye as Construction Worker

Eldridge Hyndman as Construction Worker

Jung-Yul Kim as Construction Worker

Martin Doyle as Cake Contest MC