I know you spent a lot of work on this, so i'll try to be nice here. Well, I can spot two big problems. First, your joke basically repeats itself throughout the article. That rocks, this sucks. I sort of got the joke after the opening, and the rest of your article seems like filler. I'd recommend being a bit more diverse with your jokes: why does this suck? Be more realistic with your reasons. Don't just say he got all Fs, say why he was dumb. Take a look at Guildy's Peyton Manning and Tom Brady articles- notice how they explain and joke at the same time? Go along the lines of "this sucks. How many dates did he get when he was a kid? Oh yeah. None. Your second problem is that your sections are very short, which i'll get into in the P&F section.
Your concept is very flexible, and can be expanded into a solid article. However, you need to make sure you have the right direction. Don't just repeat that this sucks. Like I said above, go more in-depth as to why he sucks. What was his childhood like? His highschool years? Is he a specific famous person. Another idea you could have would be to have another section that says the opposite: why that sucks and why this rocks. You've got a good idea, but you need to make sure you give us a good idea of who he is. On a related note, does it have to be a he? You could portray that as a boy, and it as a girl, and maybe take a sexist tone. Just an idea.
Prose and formatting:
T o o m u c h w h i t e s p a c e! Sections that contain only a few words aren't really don't serve much purpose, and make your article look unbalanced. I'd recommend taking your last few sections, and either get rid of them or greatly expand them. Maybe you could use your sections for an autobiographical tone. Anyways, just make sure you have an even amount of text, and enough images so that your article is easier to read (more on that below).
Quite simply, you don't have enough of them. You give us two random guys, and we're left to assume that they're this and that. However, there are quite a few ways you can go image-wise. If you don't reveal who this is, maybe steal the opening image from Dear Diary. You may also want to use some famous celebrities that might be considered this or that, or maybe you should take a picture of someone that looks like a loser, and portray said person as this. These are all just ideas, so make sure you stay open minded.
My overall grade of the article.
Your article, sorry to say, isn't really very funny, because you stick to one joke and rarely branch out beyond it. To recap, the best things you can possibly do is to expand it, so that it covers more areas and topics. You could sound like idiot trying to defend something he knows nothing about, or you could write a two-sided debate where two people try to rebutt each other- the possibilities are endless. I don't think this should be on VFH right now, as I think you need to keep working on it.
Bottom Line: Expand your concept and possibly change your execution. Good luck! =)