I just use two hands, one holding the ring and the other with a rag holding the stick. I aim the tip directly in the hole and it goes through without trouble. I never use the plate that is beside the hole, sometimes people use that to guide it through, but it never works for me.

One note of caution, do not put too much oil in it. You can also do damage by putting too much in it. As long as it is between the add and full marks is good.
I always check mine after it has sat all night, before I start it in the morning. That way all the oil has drained down to the crankcase.

Thanks, I'll keep that in mind...will the excess oil eventually burn off? I don't expect my high level of oil is going to last long since I'll be changing the oil this weekend when I get home...I should be okay right?

It won't really "burn" off per se. If you overfill it by too much it can cause aeration of the oil making it less effective. It can cause problems in cars but ususally it's not a big issue. On higher reving motors like motorcycles that commonly rev between 11,000 and 16,000 rpm it can cause some real problems though. Just fill it up to the recommended level and check it when you fill up your car.....that's what I do anyway.

+1, good answer.