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1.
Similar to Wingman, a WingMilf is the attractive older woman who accompanies you to bars and nightclubs as a platonic friend and in doing so increases your chances of meeting available women.
A WingMilf can make a man seem more attractive and safer to other women, because some women may judge a man's suitability based on the woman he is currently with. So basically if a man is with a very attractive woman, other women will assume he is more likely to be an acceptable candidate for a relationship. The WingMilf expands upon this concept by also presenting the man as being a safer choice. One added benefit is that a WingMilf can "talk up" the man to the other women, thus aligning with the stereotype of a mother trying to set her son up with a "nice girl".
By myself I would not have had a chance, but with Monica as my WingMilf, the ladies were practically lining up to meet me!
by MikeinVA April 01, 2009