air conditioning problem

This winter my heater's blower began to intermittently stop, sometimes coming back on by itself in a few seconds, sometimes in a couple of minutes, sometimes several minutes. It will do the same thing in max cool air mode. I bought the truck this winter, so really never had an opportunity to check how the air conditioner worked, but ran it a couple of times when the temps were a little higher...in the 40's or 50's and it seemed to blow out air quite cold enough. Yesterday it was near 60, but the AC air coming out the vents never got cool, and of course the blower still periodically stops and restarts as if there is a loose connection somewhere. I got an air conditioner testing gauge out of the garage and put it on the low side and it registered too high of pressure, "in the red." Does anyone know what I could have going on here? Are these two anomilies related? I did notice when I was checking the pressure, that the compressor never did kick in, so I probably shouldn't expect that I should have cold air if that doesn't happen.