Our story is all about a boy named Will Grayson. And another boy named Will Grayson. Confused yet? We've got you covered.
The first Will Grayson lives in a Chicago suburb and has a best friend named Tiny Cooper who is (1) extremely huge and (2) extremely gay. Will also may or may not have a crush on Tiny's friend, Jane. Sure, Will thinks she's cute and wouldn't mind going out with her, but he doesn't know if he could make it through the eventual heartbreak at the end. Oh, love.
Aside from all the drama with Jane, Will also isn't too thrilled about Tiny Dancer: The Tiny Cooper Story, the upcoming semi-biographical musical Tiny is planning to write, direct, and star in at their high school. Will is already feeling a little let down when he, Tiny, and Jane go into Chicago to see a concert, so when Will can't get in with his fake ID, he decides to do the next best thing—go buy some porn.
The second will grayson (we'll write his name in lowercase letters to distinguish him from the other Will Grayson) also lives in a Chicago suburb, but he has some different problems. Not only is will struggling with depression, but he's also in love with Isaac—a boy from Ohio he's only met online. Ugh.
Meanwhile at school, will's friend Maura is constantly trying to flirt with him. She also kind of wonders if will is gay, which he neither confirms nor denies. When Isaac suggests to will that they meet in downtown Chicago at a place called Frenchy's, will is over the moon. That is, until he realizes that Frenchy's is a porn shop.
And here's where the stories of our two Will Graysons intersect. They both meet in the porn shop as will realizes the horrible truth—Isaac isn't real. It was just Maura pretending to be someone else online. Ouch.
After the concert, Tiny and Jane meet up with the two Will Graysons and Tiny takes an instant liking to will. By the end of the night, the two boys are kissing in Millennium Park. Will and Jane also lock lips for a bit, but then Jane confesses that she's actually thinking of getting back together with her ex-boyfriend. Guess Will missed his chance.
The next day, will and Tiny are dating. Will and Jane, on the other hand, are not, which really bums Will out since he has finally realized how much he likes her. In response to these new developments, Tiny decides to rewrite his musical to be more about love, and Jane and Will discuss Schrödinger's cat, which is way more romantic than it seems. Finally Jane realizes that Will is behind a special little romantic gesture from the night of the concert and decides to give him a chance after all. Aww.
But sadly, things aren't going so well for will and Tiny. will ends up breaking up with Tiny, which just makes Tiny feel sad and unappreciated. His relationship with Will isn't much better since Will is pretty sick of playing the supporting role in the story of Tiny's fabulous life. Eventually, the two best friends are able to bury the hatchet as Will admits that he really does love Tiny Cooper—in a totally platonic, best friend kind of way, of course.
On the opening night of Tiny's musical, will grayson decides to show up to tell Tiny Cooper just how awesome he is—by getting a whole handful of local Will Graysons to come see the show. At the end of the musical, will stands up and tells Tiny how much he appreciates him, and the other Will Graysons follow suit. Then the non-Will Graysons join in as well. Everyone loves and appreciates Tiny Cooper and all is right with the world of both Will Graysons again.