Coolness belongs to a second era of old school ZZT game design: one that came after the original Town of ZZT style, and died off around 1998-ish, as far as I can tell. It's a genre where every computer will fry you if you input a bad password, where purpose is sacrificed in lieu of having objects do odd things, where you sometimes have to touch objects twice to notice something odd about them, and where sometimes, just sometimes the author put a lot of work into cheat-proofing the game and it just comes off as kind of snotty and creepy. (My favourite quote: "You didn't think I'd find out you used a cheat code did you? Well, you will die for this betrayal." ...WHAT?) If you can put up with those pratfalls, you get to see and do a few interesting things and try some interesting puzzles.
You begin Coolness as Fletcher Long, probably a sixteen year old kid, sitting in a bank after helping out his father Marshall (manager of the bank). None of the tellers talk to Fletcher, and he wanders out of the bank and onto a road to pick up items and use them on other items for no apparent reason. This is another game where the main character will throw a hissy fit if you try to travel along a clearly placed road that actually has nothing beyond it. So the only places you can visit are along this road and inexplicably through a top-secret base located behind the backyard. Coolness is a branching game like Code Red, but here, you can FEEL when certain branches are being cut off, and it's intensely annoying.
I'd rag on some of the stupidity contained in Coolness, but the fact is you should be able to reach at least one of the endings without much trouble. The graphics are very similar to Code Red and Sivion, two contemporary games Coolness is very similar to. Be aware that there are a couple of bugs (the game forgets to increase the gems variable when you search an object, then kills you if you cheat ... another reason to never put anti-cheat crap in your game.)
Coolness is decent but it also shows the weaknesses of the branching design trend started with Code Red. In Town, you could go to any of the four areas, but you saw them all by the end of the game. Instead of one solid adventure, you get several diluted ones that all begin the exact same way and typically end with the same schtick. It's not a bad game, although it could be much less obtuse.
(A much cooler game by the same author: Warlord's Temple)