Sounds like you need to take a step back and take a deep breath, Squirrles. I don't take advice very well when I'm down, so whether you decide to be receptive to any of this is up to you.
First of all, know that everybody has periods in their life where they feel depressed or unfulfilled. All of us--and I mean EVERY last person on this board--has felt the same way at some point in our lives. It's the unhappy times that make us appreciate the great days or weeks that much more. Yeah, it's a cliche, but it's also very true.
I sometimes get caught up in prose, type a lot of words, and end of saying very little of value, so let me get to the point.
If your not having any fun out at the clubs, don't go to them until you feel you can! Believe me, I sympathize with you about vapid women, I really do. But expecting much in the way of intelligent conversation at a nightclub is a bit of a stretch. Go bowling instead, or check out the new exhibit at the museum instead of going out for the same ol' friday night at the bar. Try and break out of your routine.
And who the hell cares about some dumb challenge? If it's putting pointless pressure on you and adversely affecting your lovelife, then simply don't participate. Also, you really shouldn't have as high expectations at the nightclub as your appear to hold. It's a ****ing bar! There are some nights at the bar or the club when I spend almost no time talking to women and instead spend most of the night people watching and laughing my ass off at the absurdity of it all!
One of the main pillars of the DJ philosophy is "Woman should never be the major focus of your life" Have you been observing this creed? It your frustrated or bored with women, take a few days--or a little longer--and invest your energies in your hobbies, freinds, family, education, etc. Personally, I often find am at my best picking up women on a saturday night if I spent friday night out with my buds and thursday night reading classical lit or a stimulating book on classical economics. It's all about balance