One of them is friends with Tiny Cooper – a huge gay football player who’s writing a musical about his life (later on it becomes about love).
The other lives with his mom and is chronically depressed. He has a destructive friendship with Maura, which eventually leads to meeting the first Will Grayson, Tiny Cooper and Jane.
The writing style is very distinct between chapters: Levithan writes completely in lowercase, which he explained as being Will Grayson’s perception of himself and also the way he prefers to communicate (online, via instant messaging).
The story is all about relationships – with others as well as with yourself. It’s about feeling comfortable in your own skin and about giving love a chance.
They touch subjects like homosexuality and depression with lightness and wit.
“When things break, it's not the actual breaking that prevents them from getting back together again. It's because a little piece gets lost - the two remaining ends couldn't fit together even if they wanted to. The whole shape has changed.”
“i think the idea of a 'mental health day' is something completely invented by people who have no clue what it's like to have bad mental health. the idea that your mind can be aired out in twenty-four hours is kind of like saying heart disease can be cured if you eat the right breakfast cereal. mental health days only exist for people who have the luxury of saying 'i don't want to deal with things today' and then can take the whole day off, while the rest of us are stuck fighting the fights we always fight, with no one really caring one way or another, unless we choose to bring a gun to school or ruin the morning announcements with a suicide.”
“I think about how much depends upon a best friend. Then you wake up in the morning you swing your legs out of bed and you put your feet on the ground and you stand up. You don't scoot to the edge of the bed and look down to make sure the floor is there. The floor is always there. Until it's not.”