in which the teacher struggles

As a brand-new teacher, I'd like to think that a small part of my educational philosophy goes something like this: "To encourage young minds in the skills of critical thinking, analysis, and persuasion." I truly do want to see my students think on their feet and defend their own positions on topics as varied as they are.

I just cannot, for the life of me, figure out how to grade essays in which the argument is based on flawed logic.

I have a particular student in mind: one of those pensive, quiet thinkers who doesn't say much until questioned and then you realize they've absorbed every word you've said. He's a sensitive young teenager with an uncommon sense of right and wrong. This kid is so black-and-white, I feel like 8 shades of gray, pale next to his resoluteness.

He wrote an essay this week on the topic of homosexuality and gay marriage. He fulfilled all the requirements of the essay: length, format, proper sources; he took a position and he argued it, which is exactly what I asked for. God love him, that's a tough topic for most, not least of all, such a young student. I truly admire his pluck.

It's just that the majority of the argument was ineffective; based on assumption, not fact. His suggested solutions were improbable. While I respect him and the topic he's trying to tackle, I have to strike a balance of feedback somewhere between "That's absurd" and "Good for you for making the attempt."

[In a brief but requisite disclaimer: this has nothing to do with his views on the topic, and everything to do with the logic he uses to argue his position.]

CALLING ALL TEACHERS: How do I continue to fulfill my educational philosophy and support this student with enormous potential while, at the same time, pushing him towards a higher level of analysis? How do I encourage him truthfully without crushing his spirit? (because crush I most certainly could.)

At Wheaton, my English profs would have written me a brief but gut-punching marginal comment and I would have reworked my argument by returning to commentaries by accomplished scholars, borrowing logic, and developing a critical but compelling argument of my own. But this is high school. He's 14.

I'm in over my head here. Help.