Josh Dragol is your average senior in high school. Well, he's the most average in his friend group, at least. Although he suffers from his own social anxiety, Josh is also friends with an autistic man named Jack Korus, and a lady with ADHD and depression named Faithe Pond. All of them are great friends, they understand each other and the hardships they go through.

One day, Josh finds himself in the middle of a snowstorm in the middle of nowhere. While wandering around aimlessly, he bumps into a woman named Isabelle Latem; or as she prefers to be called, Isa. It's love at first sight for him, and his world around him changes forever.

Now, Josh must balance his love life, his friendships, and his own troubles. And as he discovers more about himself and the world around him, that only gets harder as time goes on. Winter's Lament follows the story of Josh Dragol and Isa Latem, as they both go through struggles they've never faced before in their lifetime.