I have a fairly new horse that seemed impossible to
bridle. Everytime I would try to put the headstall over his ears he would turn
into 'Cosmo the giraffe', putting his head up in the air as high as he could.
Since I'm only 5'4 this became quite a problem. But I found out I could trick
him by putting the bit in his mouth first and then while he was distracted
chomping on it, I could slip the headstall on real quick. You might try
that before you buy him and see if that works for you.