The novel follows the life of two boys with the same name: Will Grayson.
Will Grayson, a boy living in Chicago, has a best friend that he has known for most of his life, Tiny Cooper, who also happens to be gay. Will shows the reader his philosophy from the very beginning of the novel: don't care too much and 'shut up' so you don't get hurt. Later, it becomes evident that Will found a liking to Tiny's friend, Jane, but is doubting doing anything about it due to the heartbreak that it could eventually cause. When Tiny reveals his plans about his upcoming semi-biographical musical that he has been writing, 'Tiny Dancer: The Tiny Cooper Story', and that he wants to direct and star in it at their high school; Will isn't too excited.
At the same time, the narration follows will grayson, a boy also living in Chicago and writing in all lowercase letters. From the very first sentence, it becomes evident that will struggles with depression and other possible mental illnesses. Moreover, he spends most of his time online, texting a boy named Isaac, who's supposedly from Ohio, but the reality of the situation is that will falls in love with a boy who doesn't exist.
One crucial night, after Will was refused into a concert due to the inauthenticity of his fake ID, he decides to go into a porn shop, which is where the two boys cross paths. will realizes that Isaac isn't real, and that Maura, a girl that he began to consider a friend, was pretending to be Isaac online. When the concert ends, Tiny and Jane meet up with the two Wills. Immediately, Tiny starts liking will. As the night progresses, Will and Jane share a kiss only to find out that Jane wants to get back with her ex-boyfriend; at the same time, the two boys (will and Tiny) end up kissing in the park. By the next day, they are already dating. As a result, Tiny makes the decision that he should rewrite his play to be more about love - a symbol that is also present in a conversation between Jane and Will at the same time, discussing Schrödinger's cat, evolving into Jane deciding to give Will a chance.
The novel progresses and will becomes overwhelmed with Tiny and his flamboyancy. This ends up in their break up and an argument between him and Will. By the end of the day, however, they manage to sort it out and admit just how much they truly care about each other and their friendship. The novel ends with the opening night of Tiny's play, where will grayson shows up to reassure Tiny by finding each Will Grayson in the local area and asking them to show their appreciation of the boy. All levels out at the end, and the two Wills find happiness in their own lives.
