Is there a correct way to put on iPod ear buds?

I always have issues with these too! I usually put them in, the left one in the right ear and the right one in the left ear, and have the sound output part facing forward. It works a lot better for me because my ears are really really small, but it still hurts anyway.

You could try getting those cushy ones that are round and long.

I gave earbuds up for larger headphones. The advantage of this, besides no more pain, is that people know to leave me alone when they see the 'phones.

Try putting them in upside down. That will sometimes help.

Get a Zune HD. Problem solved. :D

I don't like the cheap IPod earbuds at all, they either fall out or hurt like hell no matter what. I bought a pair of Sony ones for $15 and they sound better and clearer and fit better.
(Iz gotz a cowonz s9z)