"Hail the Squash" is a romantic comedy about Bumbershoot, a fresh-out-of-high school kid that is virtually invisible to everyone until one day his only friend, Hannah, blackmails him into competing in the small town's local pageant to prove to everyone once and for all that "it's what's inside that matters"... And it doesn't hurt that Bumbershoot's dream girl, the gorgeous Brittany, will be his main competitor in the pageant.