I'm not sure this is a story for the screen, for the page maybe but as it is now it sounds entirely un cinematic.
What does ?"...overcome his irrational fear of speaking..." look like? How is this a cinematic action for the screen?
In addition I think the idea of a shy boy needing to overcome his fear of talking to girls is rather mundane, it's very common amongst boys.
Lastly what are the stakes? To miss out on a date with this girl? well that is pretty much a normal event in a young man's life. It's through many of these that most men learn to overcome their fear, but these lessons are completely internal and subjective - they don't make for good cinematic stories.
I think best if you devise a plot that will ether be ?metaphor for the transformation in this story or draws a clear analogy to similar?events that so many have experienced in real life.