Shop around. I have quite narrow ear canals and found it very helpful to have the foam plugs with like a firmer plastic stem in the middle, they call them no-touch, less fiddling with rolling the plug small before shoving it in. I found mine in a pharmacy, got to pay $12 or so for a pair but they were better than the standard foam ones. The ones on the link and image below are similar to mine, you get the idea:
https://3m.ear-plugs.org/single-use-...ext-touch.html
The other trick is to reach with your left hand round the back of your head and pull your right ear backwards - it straightens the ear canal and makes plug insertion easier.
Sometimes your difficulties can be because you don't realise the direction your ear canals run. In some people they run straight in or slightly towards the front, mine slope upwards by some 30degrees which is great for not getting your ears filled with water in the rain or too long after a shower, but if you use a stethoscope you have to bend the earpieces to be in line with your canals or you'll hear less well.
The luxury comfort version which work best are moulded ear plugs from the audiologist, which rest snugly in the conchal bowl and extend a bit into the ear canal. Can also be combined with ipod earphones which will be very confortable and useful for long haul flights too.
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