Awkward Ed Wallis (Nat Wolff) moves to a new town with his single mom (Sarah Silverman) and needs help fitting in. Brainier than his peers, Ed figures playing high school football might be good way to make more friends, but his only new friend Eloise (Emma Roberts) thinks it's odd.

When Ed gets an assignment to write an essay about someone from an older generation, he introduces himself to his neighbor Ashby Holt (Mickey Rourke) and the two embark on an unlikely, immediate friendship. Ashby's style of tough love takes some getting used to but, over time, Ed learns a lot from Ashby, including how to be courageous... which is very much needed when he learns his new best friend is a former CIA assassin.