In W. D. Wetherell's story "The Bass, the River, and Sheila Mant," what obstacle did the narrator have to overcome?

“The Bass, the River, and Sheila Mant” is a coming-of-age story by W. D. Wetherell. In the story, an unnamed fourteen-year-old narrator is smitten with a crush on the beautiful seventeen-year-old Sheila Mant. The first obstacle for the narrator is overcoming his own social fear: beautiful women can be unintentionally intimidating, especially if they are a little older, so the narrator must overcome his own insecurity to summon up the courage to ask her out.

After spying on Sheila for a good portion of the summer, the narrator decided to take a chance and approach her:

It was late August by the time I got up the nerve to ask her out    . . . the only part I remember clearly is emerging from the woods toward dusk while they were playing softball on their lawn, as bashful and frightened as a unicorn.

After making a little bit of small talk, he asks her to go see a band play and she accepts, probably more out of boredom than anything else. The date is a bust, as Sheila doesn't even stay with the narrator, but instead leaves the concert with a college rower named Eric Caswell. However, as is usually the case in stories like this, the narrator learns a valuable lesson about remaining true to one's self.