Originally Posted by SlammedSL1
I was talking about me having my friend in the headlock just to clear things up
I thought that was the case. Look at the second part of my original reply, and that should cover your first option.
In that case, don't stay upright with the person as (according to what has been noted above) you can be thrown. First I would step forward (to bring their center of gravity away from them) and sit out to flatten them on their stomach. From there you can work a Bulldog choke or neck crank (even both at the same time). You also have these options from that position:
1) You can pull your hips around and take their back. From that position, you have a plethora of options to work with.
2) You can pull across side and secure their near arm with your legs for an armbar. In which case, you can work for the armbar while controlling their head. Or work a combination choke and armbar (think the "Crippler Crossface" and you will get a clear picture of what I'm talking about).
Now if you step forward and they step forward with you, you can secure their far arm and turn them over your hip to bring them down on their back in side control. With their arm secure you have a few options:
1) Step over with your far leg and secure a juji-gatame/cross armbar.
2) Secure their near arm with your legs and work either an armbar across your thigh, or an ude-garami (bent armlock/keylock) with your legs.
There are probably a few other options, but I think this is enough to work with. Let me know if you need clarification on any of the above.