The Love Song of Charlie Beecher (2016)

Charlie is an outsider who wants to fit in, so he decides to ask Kate to the prom. He must overcome his inexperience with girls, his fear of rejection, and his nemesis Bobby, the jock who already has plans to ask Kate. Charlie takes heed of Prufrock, a gentleman who has failed all his life to find love and acceptance. Charlie has one last chance to ask Kate, but will it be too late to get his date?