Is it me, the tire pump, or all the valves??!?

[Chile Pepper]

You shouldn't have to pump them up for every ride, unless it's a long time between rides?

Beg to differ here. I pump up my tires every single time I ride. No more pinch flats.

As to the pump question, I have this problem, too. Sometimes the air clearly isn't going into the tire, but rather is locking up inside the pump. I remove the pump head from the valve, release a little air from the tire (to make sure there isn't an air lock), reattach, and try again. It can be very frustrating. It's definitely the pump head, not the valve, as it happens randomly on different valves. It doesn't seem to happen to my husband though, so I assumed it was just me somehow, perhaps not getting a proper attachment to the valve. Alternatively, there could a demon living inside the pump, who has it out for me.