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if there is a 2 set i think aproaching with your wing is cool. it's worked for me at least
Yea approaching a 2 set with your wing is fine, but approaching a 2 set alone says a lot more

This is true. Women generally feel crowded at first if you approach in even numbers. Some more than others. After opening and stacking etc... you can then bring your buddy/wing over or use him as a time constraint saying you gotta go talk to him for a second. It is also not a good idea to have him approach with you because if your friend is:
A. not very good at approaching/maintaing a conversation with girls or
B. is not familiar with sarging
then generally he we will be more of a disturbance than anything else. If he is friendly, and open and has a personality, that would help, but it is still better to approach alone. He can come in handy if there is an AMOG in the group or other males as he can talk to them whilest you isolate the target.