A Pulitzer-winning writer grapples with being a widower and father after a mental breakdown, while, 27 years later, his grown daughter struggles to forge connections of her own.

NOT COOL follows former prom king and college freshman Scott (Shane Dawson) who has just returned home for Thanksgiving break only to be dumped by his eccentric, long-term girlfriend. With his world turned upside down, Scott strikes an unlikely friendship with former classmate Tori (Cherami Leigh), an ugly duckling who blossomed in her first semester of college. Together, the two embark on an outrageous adventure through their hometown. But when Scott and Tori find their friendship turning into something deeper, they realize that a few months away may have changed them more than they realized.