Ok heres what I want to do...

Ok on my computer, i use regular speakers for music/games (World of Warcraft specificly) and those are plugged into the back of my computer. Now I picked up an internet chat headset, which I have plugged into the front of my computer, so I can talk to my buddy on Skype while we play, and I have two goals. First is to get the Headset working (its an Altec Lansing Mono Headset) as I cannot get any sound or the microphone to work. The next is that I want to be able to have the gamesound and general computer sound coming through the speakers as it usually is, and have Skype Voice coming through the headset. I am sure there must be someway to get this working, so if anyone can help me out, that would be great! Thanks!

Ok, realised that what I wanted wasnt possible, but I did get the microphone working!

If you have a usb headset that's recognized as a separate audio device it's possible. I use my ps2 headset and I have the same setup you described you just have to make sure they are two different devices so you can select them in the settings.