I'm not very certain what the issue is exactly. I may have damaged the threading as, when I initially began screwing and unscrewing the drain plug I was unaware of it needing to be "pulled" so I instead screwed it even when it was "out." At this point I can't seem to get it back in.

From my knowledge it needs to be pushed in and twisted. If I want to remove it, the drain plug needs to be pulled and twisted. Now, I have it removed but I cannot get it reattached.

This is what it looks like
http://www.autopartswarehouse.com/de...e&apwidjGfT9KH

In short I'm curious if I am doing it wrong or if I ****ed up something?

 

Try using some silicone spray and then push and twist.

 

Attempted with silicone spray, on the inside and on the plug itself. It will not catch on the threads or anything. It seems to just 'turn' instead.

The leak was not subtle this time, when testing to see if it was truly sealed or not it was a very obvious pour out the hole the train plug covers. Any idea how to remedy this? New radiator? New drain plug? Maybe something else?

 

If the drain plug will not go back in, Then its time to replace the radiator. Sorry

 

Thanks master_tech! I began to remove the radiator, got the fan assembly off, the big hoses, and the four bolts. On either side of the radiator there are two hoses that appear attached to the radiator or so; metal hoses that at least one side to be air conditioning hoses. I'm not sure how well I explained this but I'm curious, how do I remove the radiator past these hoses that seem to still be holding it in place?