When I attempt to do pushups, my wrists literally fail on me after four or five. Very painful. Probably carpel tunnel or something. I used to be able to knock out three sets of twenty but now it is very painful. Oddly, I feel no pain when benching or doing military press. Is there a way to do pain free pushups without my wrists going out?

JSF is great. The more I read it, the more I want to (and slow am) change my lifestyle!

You might try getting a pair of push-up handles. Alternately you could try to train your wrists up to handle your bodyweight by doing short sets (e.g. 10 sets of 3 reps) or lightening the load by putting your knees on the floor a few reps before your wrists usually give out.

Same thing used to happen to me frequently. I could barely even get my hands in position before my wrists started to hurt. The usual cause of this is that your chest and upper arms have outpaced your wrists in terms of strength. Work on building wrist strength independently, and eventually they should catch up with the rest of your body. Obviously you need to be very gentle with them, as a strained wrist is going to interfere with, well, just about everything.
Start by loosening up your wrists.. clasp your hands up in front of your face, fingers interlocked, with your forearms close to together, and slowly rotate your hands around each other (if you're anything like me you'll probably hear a lot of clicks and pops :/).

I like to use a cheap pair of $3 hand grippers, and do about 3-5 sets of grips at the end of my workout. I alternate between doing either repeated grips to failure (squeeze together then relax, stop when it becomes very difficult to make the handles touch), or squeezing and holding the handles together for about 10-15 seconds before releasing. Try to keep your forearm and wrist comfortably aligned while doing this (helps to hold your forearm parallel in front of you while facing a mirror, and try to keep the bottom of your forearm forming an almost straight line with the bottom of your hand).

This will help build grip, wrist, and forearm strength, which in turn ought to give you better pushups, pullups, benchpresses.. lots of stuff, really. Grip strength is kind of like the tires on a car.. all the power may be in the engine, but it's all gotta go through the wheels to get anywhere.

If you want to build additional forearm strength, you can try barbell wrist curls (http://www.exrx.net/WeightExercises/WristFlexors/BBWristCurl.html). Start with a very light weight to gauge difficulty. I usually do 3 sets of 12/10/8 reps. For this exercise you probably don't want to go all the way to failure your first few sessions, as the wrist strain increases exponentially. Another way of doing this is to stand up straight with a barbell held behind your back, just under your butt, palms facing behind you, and curl the bar up and down with your wrists (really squeeze your forearms at the top). Good luck!

I've never been good with push-ups either...

Try this. It is a martial arts exercise and should help you build up strength to get ready for doing push-ups reliably.

Instead of using your hands to do a push up, simply lay down on your stomach and hold yourself straight with your toes to the ground, back and stomach straight with your upper body supported with your for arms in front of your face aligned with your ground. Most of the weight should be spread out. Don't try to do any up and down movement, just hold for a reasonable time, then repeat twice.

I believe this should help you a little bit in building up general strength. Loosening up your wrists like the above poster will help too, but do it slowly and carefully. Especially if you have possible other medical issues with your wrists.