The story begins with Samantha (Julianne Nicholson) breaking up with Allegra (Elizabeth Reaser), a lesbian author who has had relationship problems in the past. Allegra meets a man named Philip (Justin Kirk) at a party, with whom she feels a connection. The next day, she meets Grace (Gretchen Mol), Philip's ex-girlfriend, although Allegra does not know about it. Allegra and Philip begin seeing each other, and Philip leaves Grace for good. Allegra sees Grace at a convenience store and Grace cries about her boyfriend leaving her. Allegra goes on a date with Philip, but she leaves after thoughts in her mind tell her it's wrong to be with a guy. She then visits Grace at the glass factory where she works. After talking for a while, the two proceed to Allegra's apartment to have sex. Allegra goes back and forth on dates with Philip and Grace. After several more dates, Grace shows Allegra a picture of her ex-boyfriend, and she learns that Philip and Grace were together. Philip and Grace go out for dinner, where they reveal to each other that they're seeing someone else. Meanwhile, Allegra caters at a party, which turns out to be her ex-girlfriend Samantha's engagement party. Philip and Grace show up at the party, and they both discover that they have been seeing the same woman. In the end, she ends up with Samantha and never sees Philip and Grace again.