Yes, I know how to pickpocket and I know how to plant things on people. I have the ring, I activate pickpocket, I hit x to plant the ring on him and all it will do is either equip or unequip the ring on ME. I have no idea why it is doing this as I know I am doing it right (if somebody would explain in great detail (though I think I just did) how to plant this ring JUST in case I AM doing it wrong, I would be grateful). I can't figure out if this is a glitch, though I am starting to think so. I am extremely frustrated. I can not find this glitch on google anywhere and I'm reluctant to re load and try again as I have already stolen both pairs of expensive boots and the helmet and can't seem to get lucky again and not get caught (tried about 4 times). I refuse to walk away without those boots (I don't need them, they will just look pretty on my future shelf in the house in Whiterun).

So, that being said.. if I am screwed, is there any harm in ending the quest in another way mentioned (I think it was by dropping the ring and then talking to the quest giver?.. I can google that part.)? I heard it will just end the quest but nothing bad comes out of it and you can still join the thieves guild. Should I just give it up and move on?

Has anybody else had this problem? If not, let me know what you think I should do. I am not new to the elder scrolls so I don't think I'm pulling a new player mistake here..

Push square instead of X.

Square on the PS3 controller is in the same place as the X on the Xbox controller. It might pay to ask which console the OP is playing on.

Which console are you playing on xshmoopiex?

Also, wouldn't these count as spoilers? Or not really?

I suppose it would technically matter which console, but the point remains the same.

The button to "steal" is different than the button to "plant"

The "steal" button when viewing someone else's inventory, is the "equip" button when viewing your own inventory.

I doubt this counts as a spoiler, its the "initiation" quest.

OP, try to reload a save?