Lullabye Before I Wake (2008)

Billy is a senior in college. He has a vaguely cynical view on life, and has never had a girl friend. Frustrated with the monotonous routine of his daily life, he signs up for a beach trip, where he ends up meeting a free spirit named Megan. As they continually bump into each other at school, Billy finds himself falling in love. His roommate Johnny warns him that he's losing himself in his obsession for Megan. Billy's frustration and confusion grows as he tries to figure out how she feels about him, his emotions finding an outlet in his increasingly dramatic dreams.