 After a significant break from dating, Jess develops a flirtation with Annie, a waitress at the coffee shop near Jess's work.Eventually Jess asks her out, and they have a date at Annie's house; before they have sex, Jess is able to slip into her strap-on without Annie noticing, effectively passing as male throughout the encounter.The next day, Jess accompanies Annie to a family wedding, where Annie makes several homophobic comments about the visibly gay man in attendance.