Mystery Method has alot of good tips for how to wingman.
In my experience we decide who is going to open the set and then the wingman comes into it after attraction has been built a little.
My mates and I often give each other titles to introduce each other.
For example...
Wingman:Hey have you met my buddy Giacomo? Yeah he is about somewhere, his fashion sense is incredible, they did a story on him in "Alpha" magazine!!! (It's not lying, its flirting)
HB: BLAH BLAH BLAH
ENTER GIACOMO
Giacomo: Hey wingman there you are buddy. I was looking for you, HB says she wants to meet you (or some other DHV)
HB: Hey your that guy they did a fashion story on!
Giacomo: My fashion sense is only exceeded by my charm
HB gets her friend and we all go home for an orgy. (Or something like that)
It's not about appearing more confident I don't think.
I think it's just about not being intimidating, or being like every other guy who approaches with his friends.
And bringing in the wingman later is perfect because straight away he is DHV'ed (he is with you) and can start working on the obstacles.