In this coming-of-age romantic comedy, a 17-year-old virgin film nerd, Joseph Caldo, who sees himself as a real-life art film, experiences first love, first sex, and first heartbreak in the surreal setting of South Florida while trying to make sense of Shakespeare’s stupid plays.

Caldo has no real social life, unless arguing about film online counts. Having seen so many films while struggling romantically, he has formed a theory that women pick romantic partners the way they pick which movie to watch. He’s definitely not a blockbuster, a rom com, or even a horror film, he’s more of an indie art film that is unfortunately funny. He worries he’ll never find the person who will accept and love him, the way that he accepts and loves his favorite obscure films.

That is until he meets Alexia at his grandmother's retirement home. Alexia was court-ordered to do volunteer work for her DUI but it's cool, Caldo has issues too, and it feels like they have a real connection. But there's also Valerie. The new girl at Caldo's awkwardly small school. She's a straight-A student who is attending on scholarship and is assigned the difficult task to mentor him in Shakespeare's plays. The two opposites have nothing in common except for being romantics who do nothing but fail at romance.

With first jobs that go very wrong, untimely food poisoning, and fake prom dates, Caldo unintentionally reenacts Shakespearian tropes in the heart of South Florida. Humor award-winning author, Christoph Paul, and Caroline Macon Fleischer's Shakespeare in South Florida is a quirky romantic comedy about being 17 and falling in love.