Oh man, do I remember that! I could NOT swallow pills...even the smallest ones. I used to special order every Rx in liquid forms up until I was a senior in HS!

I think for me, starting with a tiny pill, on the back of my tongue (though not too far back or you gag), and a HUGE glass of water finally got me there. The pill had to be so small that I didn't feel it sitting there. It was a mental thing as much as it was a physical one. I still have to hold my head back when swallowing pills, it's embarassing!

I've also found that certain types of pills are better than others. Solid, coated pills (like caplets) are heavy and sink in liquid. For those, I can get a mouthful of water, hold my head back, toss in the pill, and then swallow a few seconds later after it sinks to the back of my mouth/throat. That helps, because you never feel the pill at all.

If the pill is a capsule that floats (some vitamins & some gel caps), it's better to do the above, but instead of holding my head back, I hold it forward so that the pill floats to the top of the water near the back of my mouth/throat. Then I swallow without raising my head. Again, it makes me look like an idiot, but it works!