Throughout my life I've had a problem with pills. No, not that kind of problem. ;p I've just never been able to swallow them without a problem. I guess a part of the problem is because I hardly get any practice (because I keep away from artificial medicine in general), but I don't think any amount of attempts will make it easier for me. Pills just aren't natural, I can't treat them like candy, or like food, and I can't help being aware of them. Compared to everything else that I put in my mouth, a pill might as well be an alien.
I'm not even sure if the size makes it any harder or easier for me. The other day, for instance, I managed to choke one of the small Ibuprofen I was taking, but the night before that I managed a capsule easily twice its size.