have never pumped a tire properly. HELP

[MartianDestiny]

i have a hard time pushing the handle all the way down, either because i have weak upper body strength or i am small, i don't know. anyone else have this problem?

Normal (well, for us small ladies). I typically have to use my whole body to get the last 20-25psi in my tires (road or mountain, though mainly road). Yes, this means looking ridiculous as I lean over the pump and lift my feet off the ground so all my body weight is on it. You are not alone.

Your pump should be making your life easier by getting a good seal though (you shouldn't hear air escaping). May really be your pump, take it with you to the shop next time and see if they can help you get it to work with yours (rather than their $175 models that, while very very nice, aren't practical for us mere mortals )

Edited for story to make you feel better (or at least not alone):

Two years ago in a bike shop very close to you (Sunnyvale, CA) I was shopping for a mountain bike. A nice young salesman gladly pulled the XXS version out of storage in the back, of course with two flat tires. He then proceeded to try to get a good enough seal to fill the first tire for 10 minutes before finally conceding and sulking off embarrassed to get his manager to help. It then took the manager 5 more minutes to get a seal. YOU ARE NOT ALONE!!! (and yes, I've done the same thing too, finally threw the darned pump (mini pump) against the wall and broke it for good....good riddance!!)