Left alone by his fiancée, aspiring writer Kinny searches for a new partner despite the hopeless futility of online dating.
After questionable advice from a waiter, a single mother, a poor songwriter, and an unhappily-married friend, Kinny is encouraged by his flamboyant cousin Sage. Though hindered by his drinking habits and reluctance to move forward, Kinny meets Heather at an insult restaurant, and their second date is at a disappointing musical in the community playhouse.
Ultimately, Kinny faces this philosophical question: Does he need a significant other to find happiness, or will he brighten his future by building his self esteem before further dating?