Smell the Coffee (2010)

Ricky, a shy college professor finds it hard meeting women. One day he meets a man claiming to be the ghost of the dead poet, Alejandro Vincente Cruz, who urges Ricky to approach Christina, his high school crush, before it's too late. Ricky must decide whether to believe an apparent crazy New Yorker, and get the courage to speak to a woman he was enamored with.