Hayley stumbles upon a bundle of letters with an engagement ring from a mysterious sender, she decides to respond to him with her own alias, and with it start the anonymous correspondence that will change her life forever.

Josh Greenberg is a naive romantic on a desperate quest for love. When his longtime girlfriend dumps him, Josh enters the dating scene, a nightmarish hellscape of untold horror. Despite the agony, Josh continues his search in the hopes of finding someone who will make all the misery worth it.

Lonely burnout Bill Berney loses his dog, and skateboards around the city trying to find him. Throughout this sweaty summer day, Bill is repeatedly confronted with his past, and those involved in it.