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Structure
The story is told from two different perspectives, through both Will Grayson 1 and will grayson 2. When reading the odd-numbered chapters, the reader sees high school through the eyes of a heterosexual all-star athlete, Will Grayson 1. When reading the even-numbered chapters, the reader sees high school through the eyes of a homosexual teenager, as will grayson 2. Though there are two separate characters speaking, the story remains the same from start to finish. As the story progresses, the perspectives do, however, blend together into one clear and cohesive storyline, rather than two separate plot lines, within the same high school story, told by two different characters.

At the beginning of the story, it is clear to distinguish between two completely different voices between the chapters; the reader is able to decipher when Will Grayson 1 is taking center stage when he talks about the girl that he's been crushing on, Jane Turner. Will Grayson 1's chapters are told with proper punctuation and capitalization, whereas will grayson 2's chapters are filled with more vulgarity, though Will Grayson 1 is just as vulgar and crude as will grayson 2 is. will grayson 2's chapters are filled with little character scripts of both casual and digital conversations that he has with his mom, his friend Maura (who is also attracted to him both platonically and romantically), and his crush, at the beginning of the story, isaac, who goes by the alias of boundbydad via instant messaging.

As the story progresses, it occasionally becomes incredibly difficult to read, as the stories of Will Grayson 1 and will grayson 2 become entangled into each other, carrying strong themes of young love, teen angst and rebellion, and self-discovery throughout the book until the ending scene.

Dialogue
With the story's strongest focus being the musical about Tiny Cooper, Tiny Dancer, the chapters that are enumerated for will grayson 2 all follow a written dialogue that echoes that of a script, with character names preceding a colon before their dialogue is written in the text. The conversations before will grayson 2 meets Will Grayson 1 echo that of a chatroom instant message, with usernames and special nicknames for the characters preceding each of the conversation pieces. The text is written this way to help the reading audience relate to the happenings of the story better, by familiarizing the way that each chunk of dialogue is received.

Epilogue
The epilogue of this novel is featured before the title page, and is only two paragraphs long. The blurb features the exact moment where Will Grayson 1 meets will grayson 2 later on in the novel. Both shocked and surprised, the reader is able to experience the rush of shock and confusion that these two teenagers faced when they learned that they both shared the same name. The homosexual will grayson 2 is quiet, and shy, and reluctant to respond to the more brooding, masculine heterosexual Will Grayson 1. This exact scene can be dissected to understand the fear and anxiety that LGBT-identifying youth face in high school, on an almost-daily basis.

Plot Summary
The novel follows two boys who both go by the name Will Grayson. The first Will, whose POV always having correct capitalization, is described as trying to live his life without being noticed. This is complicated by the fact that his best friend, Tiny Cooper, described as "the world's largest person who is really, really gay" and "the world's gayest person who is really, really large", is not the type to go around unnoticed. Tiny is also throughout the novel trying to create an autobiographical musical, which further draws attention to himself and everyone around him.

The other will grayson, whose POV never having capitalization, goes through his life without anything good to hold on to besides an online relationship with someone who goes by the name Isaac. Intent on meeting up with Isaac, will grayson sets up an encounter one night in Chicago but eventually finds out that Isaac was invented by a girl named Maura (who is also his peer in his daily school life). What ensues brings both characters together and changes both of their lives forever in ways they could never have guessed or imagined.

Problems with the Ending
Many readers have complained that the ending to Will Grayson, Will Grayson is "too predictable." Others have expressed concerns, asking if the ending is realistic, whereas others have asked if the ending is realistic enough. At the end of the story, after breaking up with Tiny Cooper, and becoming Ex-Boyfriend #18, will grayson 2 arranges to have a massive group of Will Grayson's from around the state come to the opening performance of Tiny Dancer, the school musical about Tiny's own life as a homosexual high school athlete dancing through adolescence. Reviewers have argued that this ending seems to be "too typical," making the ending a little cheesy and deemed it as too "played out."

will grayson 2 ended his almost-instant relationship with Tiny Cooper because of will's own self-depreciation and self-loathing. Tiny Cooper spends the rest of the story, up to opening night of his musical, feeling unappreciated and unloved by those who he had both loved and appreciated. The chorus of the musical, made to mimic all of Tiny's Ex-Boyfriends (#1-18), echoes this feeling, by having their main lines reflect the lines that they had used to break up with Tiny. Due to will grayson 2's own self-guilt, he works with gideon to gather up a bunch of Will Grayson's, and even one Wilma Grayson, to all rise at the end of the play, from the audience, to take a stand against Tiny's new self-depreciation, by exclaiming that they love and appreciate him. All of the Will Grayson's, ultimately, love and appreciate Tiny Cooper.

Main characters

 * Will Grayson 1: First protagonist of the story. He lives in Chicago, Illinois. His point of view is seen in the odd-numbered chapters, where the entirety of the text shows proper capitalization. He is the first, and only, straight-identifying member of the Gay Straight Alliance. His chapters are written in the familiar tone of voice. He is obsessed with the band Neutral Milk Hotel. Though he struggles to determine his sexuality through the beginning of the story, Jane Turner soon becomes his love interest; Tiny Cooper is his best friend. He is a clear example of teen angst from start to finish of the novel.
 * will grayson 2: Second protagonist of the story. He lives in Naperville, Illinois, a suburb of Chicago. His point of view is seen in the even-numbered chapters, where the entirety of the text is always lowercased. He has a crush on Isaac, a boy whom he has never met in person; the two of them communicate via instant messaging, in secrecy, under the pseudonym grayscale and boundbydad. He meets Tiny Cooper through Will Grayson 1, and falls in love with him later on in the story. He is not the stereotypical gay teenager; he is angry, and vulgar, and is one of the few characters that readers may be able to relate to. will grayson 2 self-diagnoses himself with depression, claiming, early on, that he is constantly "torn between killing himself and killing everyone around him." He is not close with any major character in his school, though he does interact with his not-so-secret admirer, Maura.

Secondary characters

 * Tiny Cooper: Will Grayson 1's first best friend in school, they became friends again after Will Grayson 1 wrote an article in the school newspaper defending Tiny's right to change in the locker room. He is described as being a large flamboyant homosexual football player who runs through love interests swiftly. He is described as being constantly in-love, and always self-involved. He is the president of the Gay-Straight Alliance at school. He is described as "very gay, and very proud." He meets will grayson 2 through Will Grayson 1. Though the book may be titled after both Will Grayson's, Tiny becomes the primary focus of the story.
 * Jane Turner: Friend of Tiny and Will Grayson 1. She is also a member of the Gay-Straight Alliance at school, and adores Neutral Milk Hotel. She is Will Grayson 1's love interest, though she may not share the same feelings for him as he does for her.
 * Maura: A goth girl who is attracted to will grayson 2. She is one of the few people at his school with whom he interacts. She is described by will grayson 2 as "unrealistically friendly," because she pays "too much attention" to him when he describes himself as uninteresting. Maura poses as the online-love interest of will grayson 2, Isaac, to gain will's attention, admiration, and further, affection.