Back when I was a kid, they told us "Never try to put anything smaller than your elbow into your ear." Of course we laughed like little chipmunks, the image was so silly.
But in general, I do find it best to leave the insides of my ears alone. All the ear buds I've ever tried hurt, or itch, or make my ear canal sweaty... just can't get into them. I know they're super popular, but nevertheless...