After his very first date at age 15 finished with the girl making out with an additional man at a celebration, aspiring writer Lester Grimm has actually dealt with all his girlfriends with envy and also uncertainty. While dating Ramona Ray, paranoia gets the most effective of him when he discovers that her latest ex is successful storyteller Dashiell Frank. Lester starts participating in the exact same group therapy sessions as Dashiell to discover Ramona's past with him.