Untrusting of women following a bitter breakup on the eve of Thanksgiving, a misanthropic construction worker finds himself inexplicably attracted to his younger brother's new girlfriend. Caleb Sinclaire (Adam Scott) has just been through a particularly difficult breakup. Isolated, yet strangely contented with his newly single status, Caleb wears his distain toward women as a macho badge of honor. However, when Thanksgiving weekend arrives and Caleb meets his younger brother Peter's (Alex Frost) new girlfriend, Emma (Brittany Snow), his initial attempts to convince his sibling that the relationship will yield nothing but pain are quickly sidelined by his growing attraction to the beautiful girl. His vulnerability gradually bubbling to the surface over the course of the holiday weekend, Caleb is soon forced to confront the feelings that he's been trying so desperately to conceal beneath a swaggering facade.