History of the Wingman
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The concept of a "wingman" goes back to World War I when pilots found that attacking in formations provided more support than attacking a target on their own. "Wingman" was originally a term referring to the plane flying beside and slightly behind the lead plane in an aircraft formation. A wingman is a pilot who supports another in a potentially dangerous flying environment.
Wingman is a term in the seduction community that a man (or woman) may take when he goes to a club or bar with an accompanying male (or female). A wingman is expected to support his or her friend in approaching a member of the opposite sex. The men often pick a desired woman, who is referred to as the "target." The man intending to seduce the target is often called the "pilot." The wingman is expected to back up the pilot, which typically entails talking to the target's less attractive friend(s) and making comments that will make the pilot seem more attractive. This is often referred to as "taking one for the team." The 1986 film Top Gun is often credited with bringing the term into popular usage.
The wingman motivates the pilot to be social and practice approaching women. He helps the pilot approach pairs and groups of women without the awkwardness of being alone. He will sometimes take the less attractive woman of a pair so that the pilot can get the more attractive without interruption. Other responsibilities include remembering details (i.e. target's names and personal information) as well as compensating for intoxication in the judgment of the pilot.
The pilot is usually the more skilled seducer, a man from whom the wingman can learn a great deal. However, sometimes the pilot can take the role of the wingman to help out a friend in need.
The metaphor of a "pilot" and "wingman" and can be extended even further to other characteristics of flight. For example, if there are more than two friends (pilot and wingman) at a club with interest in meeting women, than the group may be referred to as a "squadron". When the squadron decides upon which girl is the most attractive, that may be referred to as "marking" or "painting" the target. Making a pass at the group of girls would be called a "strafing run". As with the Air Force, when a squadron member seduces 5 or more girls, he is then an "Ace" and is likely more than capable of being a lead in future attempts.
Of course, when failing it is called being "shot down".
Another dynamic can be set up between the wingman and the pilot, one that accrues the desired benefit to the wingman rather than the pilot. In this scenario, the wingman will spot a woman he would like to meet. The wingman may not be as skilled at opening up the group as a pilot, however, so he will enlist the help of the pilot, who will boldly approach the group and attempt to dazzle them. This will give the wingman a chance to slip in under the radar and join in the group in an understated yet still confident fashion. This dynamic works particularly well if the wingman is attempting to meet a woman who is more aware of and therefore more impervious to the standard pick-up techniques. The pilot may purposefully set himself up to be overly arrogant or boorish, allowing the wingman to swoop in and be (or at least appear to be) the more intelligent, sincere, and subtly witty one. For a team in which each person clearly has one or the other personality strength, this is a good alternate technique to make sure that each team member accrues advantages over the long haul. from Wikipedia
Wingman in Military Aviation
The idea behind the Wingman is to add the element of mutual support to aerial combat. A wingman makes the flight both offensively and defensively more capable by increasing fire power, situational awareness (hopefully), attacking an enemy threatening a comrade, and most importantly the ability to employ more dynamic tactics.
Wingman in today's Air Force has a broader meaning. However, the concept still holds true to its history in aviation. As a good wingman, you watch out for your fellow Airmen, to protect them from becoming victims of enemies such complacency, lack of discipline or accepting unnecessary risks. Taking care of your people, identifying risk factor behaviors and taking corrective actions is part of our core values. It's service before self. Safety is a Wingman.
Erich Hartmann, the Flying Ace with the most kills in history, was famous for never losing a wingman.
The USAF extends the Wingman concept to include Wingman Culture. Wingman Culture generalizes the concept of a Wingman to include Airmen helping Airmen. The wingman culture concept has great potential for Verbification of Wingman. Example: that Airman should be wingmanned.
Today's wingman concept is nothing new. Col. Francis "Gabby" Gabreski, an early Air Force pioneer who is credited with 28 aerial victories in WWII, said this:
"The wingman is absolutely indispensable. I look after the wingman. The wingman looks after me. It's another set of eyes protecting you. That's the defensive part.
"Offensively, it gives you a lot more firepower. We work together. We fight together. The wingman knows what his responsibilities are and knows what mine are. Wars are not won by individuals. They're won by teams." source here