A hopeless romantic with an insane wingman goes to absurd lengths to the win the heart of his best friend, Annie.

Michael has been stuck on Annie for as long as he can remember. When he finally asks her to go on "one official date" before she moves away, Michael gets one last chance to win Annie's heart. Desperate for a fool-proof plan, he turns to the wrong friend for advice and finds himself in a coming-of-age nightmare.