What would a normal person do? Help please!

I am a social retard.

There. Now all of you who know me can feel better knowing that I do, indeed, know what you've already figured out; and any of you who are new around here, well, it'll all just make more sense now.

As much as I'd like to go into defensive specifics outlining the exact nature of my social ineptitudeNess, I've got something of an emergency or three going on and could really use some advice from those of you in my brilliant audience who are not social troglodytes.

So here's my question:
At what point is it okay to tell someone exactly what you think of them and/or where in their life they are complete fucktards? Not in a mean way; just in the hopes that it might enlighten them and nudge them toward realizing that they might be able to make different choices and improve their own lives and those of the people around them.
Is that ever okay? I mean, I wish someone would sit me down and outline exactly what the hell is wrong with me. From their point of view. Like I said before, I know I'm a social retard, but am not always clear on why, exactly, or what to do to fix it.

Here's the situation. Any and all opinions and feedback are greatly appreciated, if you make it through this. Ahem.

I have this friend. We'll just call him "D". We were best friends in high school, in that "When Harry Met Sally" way, without the romantic ending. Just buddies. Really. He was the archetypal 80's wannabe-yuppie; he bragged that he was going to be a millionaire business/financial genius by the age of 30. He was an only child and his financially-struggling parents nonetheless showered him with the best of everything. He drove 2 Porches and wore designer clothes and was the first person in Pocatello with a cd player. Despite his deeply ingrained sense of entitlement, he was a good friend.
Flash forward 15 years. We lost touch after h.s. and reconnected via Classmates.com and facebook. We've exchanged a few emails detailing our grownup lives. He's accomplished some amazing things. Seriously. He's one of those people who wants something and BAM! does it. He attended West Point, went career military, did 3 tours of Iraq and Afghanistan, has received commendations from Senators and Brigadier Generals, has double Master's degrees and a Ph.D., and is now serving as a second-in-command over the NATO troops in Afghanistan. All of them. He's big time over there.
I know all of this because he sends out "fan letters." To the people he regards as his "fans". He forwards the internal emails between the military bigwigs praising the wonders of MGR D. I shit you not. He has very floridly regaled me with all of his wondrous accomplishments, including how he scored a hot wife and has two perfect kids.
Sounds like someone I'd be proud to call a friend, right?
Here's my problem:
He's a self-centered, arrogant little toe-rag.
In all of our exchanges, he's never, ever, not once remarked upon anything I've told him about my life. Ever. Not even when I told him that my husband trained plebes at West Point when D was a plebe at West Point and maybe they'd had some interaction; wouldn't that be some Six-Degrees-of-Separation? Nor when I told him I'm writing a novel or was a teacher or any of the little lame things I've accomplished. Lame compared to his, anyway. But he could have said something, right?
Our latest exchange was about his failing marriage and about how it's all his wife's fault. Because she's not a "Team player". As in "Team D". I sympathized, I empathized with helpful anecdotes from my own roller coaster of a marriage. To which he did not respond. At all. No "Wow, sounds like you know what I'm going through" or "My Gosh, Nessa, I had no idea of your personal struggles." Nup. Just talked over me on the IM about the shortcomings of his wife. He expressed his disgust at her daring to say that no one else would "put up with his shit". "What shit?" he asks.
Um, maybe the shit where you don't listen to anything anyone says and everything is about you? Maybe the shit where you don't give a shit what other people might need? Maybe the shit where nothing is as important as what you are needing/doing/winning right now? Maybe the shit where all you do is brag and expect everyone to sycophantically swoon at your every word?

Ok, I didn't say those things. But I want to. My question for you is: should I? Should I risk losing his friendship (or whatever this is; aren't friendships actually supposed to be two-way?) by telling him he's an arrogant toe-rag who should thank his lucky stars that this woman has put up with his shit for the last 12 years? Is this something that is normal social interaction: calling bullshit for what it is and hoping the person has an A-ha! moment because of it?
Or do I just keep smiling and deleting the fan letters and trying to have normal conversations with him?

Thank you for your time. You are contributing to an important public service with your response.

Social retard out.