So this whole “Facebook vs Gmail” buzz, to me, is very amusing. In retrospect, I should have seen something like this coming from Facebook. It is, after all, the great Satan that over 500 million people pay homage to (take note, religious start-ups). But I’ve been mulling the thought of a Facebook supported email service and I can only think of one thing: AOL.

AOL tried email during it’s run as the top internet provider. It didn’t seem to catch on as much as its instant messenger or jokes about it did. I have this sneaky suspicion that this is going to be the road that Facebook inadvertently follows.

Here are a few of the reasons why I think Facebook will fail:

1. Every couple of months, your new Facebook email will randomly resend emails you’ve sent months before. That will make it even more awkward when your ex files that restraining order. To date, “Facebook made me do it” doesn’t hold any water in a courtroom.
2. Every couple of months, your new Facebook email will randomly reconfigure your email settings, making it a bear to relearn your settings “in the interest of making the user happier”. This will coincide with many workplace committed seppuku and drag down the world economy. Meanwhile, Mark Zuckerburg will be purchasing a $100 million yacht while sipping mimosa’s and giving the world the middle finger.
3. Your new Facebook email will recommend new email friends for you, even though you don’t need new contacts. It will also recommend friends of friends, leading to more relationship problems after your girlfriend swears she isn’t friends with her ex any longer and yet you were just recommended him as a friend due to your (soon to be) previous relationship with your girlfriend.
4. Facebook email will scan your messages (like gmail) and then recommend ads on your side banners. This will cause for quite some workplace embarrassment when your latest email to your sweetie gets more than a little pornographic and Facebook mail offers you ads on viagra and other “enhancements” to your love life. From then on out, your email will always be gleefully monitored by your boss — assuming you still have a job.
5. Applications make Facebook money, so why wouldn’t it work for Facebook mail? Well, considering four times out of five those apps won’t load, it’s safe to assume that any add-ons you have for your new and shiny Facebook email won’t work. That includes that fancy little ad virus detector Facebook is advertising on your sidebar.

So do you have any examples of your own that would make Facebook email fail in the eyes of the world?