This question took me a little off guard because when I read it I realized I didn't have a good answer. Here's what Farend wrote:

My question is how do I make a story that hurts people? You know, those stories where people feel what the characters are feeling? Seeing what they're seeing? How do you make that? (Like you did in High School Tabloid).

OK, so first things first. Farend, thanks for asking such a great question, and thanks for your kind words about High School Tabloid!

As for the question, I want to start by explaining why the question took me off guard. As I've mentioned before in this book, I've been writing stories for about twenty years. When I first began, there were areas where my craft was strong and other areas where I really struggled. One of my biggest struggles at the outset was writing a story that made the reader feel what the character was feeling. And to be honest, I still wonder if I'm any good at giving the reader the feels. Making you laugh, sure! Making you think, probably. Making you feel, I hope so.

Of course, you have to do more than hope to make a reader feel, and you asked a practical question, so let me try and give you some practical advice. 

First, I think it's important to ask yourself what you want the reader to feel. Be as specific as you can. Do you want them to feel sad? Happy? Annoyed? Whatever emotion you want the reader to feel is fine. But if you don't ask that question before you write the scene or the story, you'll have a hard time getting the reader to feel anything. So, again, start with a specific goal.

Second, you need to hold yourself accountable. If you want the reader to feel sad at the end of the story, you need to ask yourself if you feel sad. And you need to be honest about the answer! One way writers talk about this is whether or not they've earned that feeling. You can describe a sad outcome at the end of the story, but earning it means putting in the character work up front so that when we get to that emotional point we're not just describing events that could happen to anyone, we're feeling the story as if it's happening to someone we love. 

OK, one last piece of advice, although I'm not sure how practical it is. I think putting the feels in a story improves with life experience. Yes, I'm a better writer today than I was twenty years ago because I've improved my skills. But I'm also a better writer because of the life experience I bring to my work. The best stories speak to the human condition, they talk about things like love and loss. We experience those things throughout our lives, but as we age we gain perspective on them. That's what I mean when I say that life experience improves my ability to put the feels in a story. So, keep writing because you'll improve your craft. And keep learning from your own life experience. Because as your craft improves, you'll draw on that experience to tell stories that resonate with readers on an emotional level.

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