look up any word, like swag:
 
1.
A wingman item is typically something you can carry around no matter how large or small that stands out and is generally intriguing. The wingman item is used to start conversations with females if you have no way of directly approaching and talking to her/them. You need to be within a short walking distance for the girl you are trying to talk to, however, unlike a wingman, you are trying to get the girl to approach you; unless you are skilled enough to approach the girl with your item in some clever manner. This 'conversation' starter can lead to one or two results depending on how well you can sustain a conversation.

1) The conversation will avalanche down and you will be able to exchange numbers or at least some information.
2) The conversation will stop after you have talked a little about your wingman item, and she may say she needs to leave due to the stale conversation.

Don't forget your wingman item is only a conversation starter, and you should attempt to change the subject with general questions to keep the conversation flowing.
-Wingman item = Chihuahua

Female "Oh my gosh he is so cute!"
You "Yea, I've had him for a little while now."
Female "Where'd you get him?"
etc.

Guitars, pictures, or anything a little out of the ordinary tend to be good wingman items as well.
by Oshu September 05, 2010