Am I being too hard on myself or should I give up completely?

[nolabear]

12. I have what might sound like a silly question.

Your post is eloquent and the spelling and grammar are fine. The exerpt does have mistakes in it, not unfixable by any means but it sounds much different from your post. Might you be trying too hard to "write"? If you just relaxed and told it as though you were telling the story to someone (like you did us in the post) it might be more naturally polished.

That said, it just looks like a rough draft and your relative-friend sounds like a massive buzzkill. Keep writing if you are a writer. And nobody gets to claim that but you.