Bicycle Tutor

I have been commuting for a few months and my headset is getting stiffer and stiffer. I am hoping that I just need to overhaul the headset. So, I started by removing the bolt, but wasn't thinking and removed it all the way. The wedge remained in the tube (of course) which I have since removed. It was really greasy, and dirty so I cleaned it, but I'm wondering about what to do when I reattach the bolt and put it all back in the head tube. Should I be putting some grease on the wedge? How about the other half of that tube. I'm assuming I'll grease the bolt. Is there a tutorial on this?
I looked over the overhaul of the headset and will do what was said for the rest of the job. I'm up for any thoughts as I'm new to bike repair and just figure out things as I go along. Will a clean of the headset/ bearings loosen things up? Thanks for thoughts.

Check out this video. At about 0:35 I talk about removing a quill stem and at about 2:53 there's some tips for re-installing and grease... hope that helps!