Prom King, 2010 (2017)

Charlie is an adorably awkward 20-year-old freshman who is attending college in New York City. A hopeless romantic, he dreams of being kissed while standing on the rainsoaked streets of the Big Apple, a soundtrack of swelling strings playing in the background. (Think Audrey Hepburn in Breakfast at Tiffany's.)
Love may be a many splendoured thing, but Charlie is looking in all the wrong places, and the men in his life offer little more than heartache and disappointment. With every romantic failure, Charlie becomes increasingly disillusioned, fearing he will never find his happy Hollywood ending. - See more at: