How to Be a Godly Wingman

What is a wing-man?

The term comes from the air-force where a pilot will have a wingman fight with him in battle. Wingmen protect each as they accomplish a mission together.  The older term for this concept is “best man.” But now “best man” is primarily a ceremonial role. The ancient term for this same concept is “friend of the bridegroom.”

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The role of wingman starts way before the wedding. In fact it can start before the relationship starts. The Wingman assists from the beginning of the relationship through the wedding ceremony.

Lets call the wingman “Walter.”

His single friend is Sam.

Wingmen keep confidences.

Sam needs a sounding board. He may need to work out how he feels about girls by talking through it with a trusted buddy. Yes ladies. Guys do talk about this sort of thing but only to those they trust. Walter listens. He gives honest feedback. Above all he does not betray Sam’s confidence.

Wingmen encourage.

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Pursuing a woman is not easy. The path to marriage for men is paved with rejection and pain. A good wing-man encourages his bother to try again even after devastating failures. Sam doesn’t need hollow platitudes. He needs hope, encouragement and prayer.

Wingmen help create opportunities.

As we discuss in other posts, interacting with godly girls in conservative communities is challenging. To overcome these challenges Sam needs Walter’s help to create opportunities to interact with God fearing single ladies. This may mean throwing parties, sending out text messages to invite people to play ultimate Frisbee or going out to eat after church.

dilbert

Wingmen show up intentionally.

So, Walter throws a party and Sam shows up and sees Sally, who he doesn’t know very well. She’s popular and Sam wants to break through the crowd and talk to Sally but he needs help.

Enter wingman.

Walter, can help by running interference for Sam by engaging the people around Sally in conversation. This helps Sam and Sally talk when they may not have had the opportunity otherwise. If Sam is shy this sort of assistance is particularly helpful.

Shy guys can make faithful husbands.
They just need help at first.

Wingmen ask intentional questions.

Courtship Wingman

So, Sam, Sally and Walter are in a group of people talking at the party.

Remember, Sam wants doesn’t know Sally well and doesn’t want to lead her on unnecessarily.  Sam doesn’t know if he likes her or not but he wants to get to know her better.

Walter can help by asking intentional questions that help Sam get to know Sally better. This is not to say Sam asks no questions. But Walter can ask the potentially awkward questions. When this is done well, Sally is none the wiser.

Wingmen leave intentionally.

Walter, Sam and Sally are now talking just the three of them at the party. This is when it may be a good idea for Walter to disappear. He may excuse himself to get punch and then get caught up in a different conversation and not get back. This gives Sam and Sally a chance to talk alone at the party which they may not have gotten otherwise.

Wingman2

Walter holds  Sam accountable.

As Sam and Sally’s relationship deepens Walter keeps Sam accountable to make sure that Sam is honoring Jesus in their relationship. Is Sam walking in the fear of the Lord? Walter asks Sam tough questions and insists on honest answers.

Wingmen don’t outshine.

Wingman #3

It is important for Walter not to outshine Sam. His job is to make Sam look good. If Walter is stealing attention he failing as wingman. John the Baptist is a great example of how to do this well. His job was to prepare the way for the bridegroom Jesus. This meant getting out of the way at the end.

Wingmen hold the rings.

It is the wingman, or best man, who stands next to the groom at the wedding. Where would the groom be without him? Maybe still single. Maybe not. Either way Sam knows he has a true friend in Walter.

“Greater love hath no man than this, that a man lay down his life for his friends.”

-Jesus

What do you think?

  • Should courtship best be done with just the man and the woman’s family? Or is the best man’s role important?
  • Do women have a similar system? Or do Maids of Honor just help with hair and logistics?
  • Have you ever been a wingman? How did it go?
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  • http://twitter.com/pbadeer Preston Badeer

    It seems to make it harder not to outshine or even unintentionally deceive the girl when the wingman is the one asking the harder questions…she can get to thinking that the wingman is the one interested.
    Any suggestions on how to avoid this?

    • http://www.thomasumstattd.com Thomas Umstattd

      Good point Preston. The point man needs to be asking tough questions too and the wingman needs to not ask to many questions.

      There are definitely some ways for guys to turn off the charm. The wingman just needs to put his foot in his mouth a few times and the point man should be good to go.

      Also if you get a wingman who already has a girlfriend or wife that can help too. That way there is no competition.

  • calebhobart

    I have to say-I am a great wingman. I naturally put my foot in my mouth.

  • Caleb Hobart

    I have to say-I am a great wingman. I naturally put my foot in my mouth.

  • Cynthia

    I really like the idea of a wing-man. I like that the guy is not alone in his pursuit of the girl. He has a trustworthy friend at his side. I also like (from a lady's perspective) that the wing-man helps the girl meet the guy. Sometimes you guys don't know it, but the girl is often really wishing she could meet the “Sam” Thomas talked about, but perhaps she is too shy too.

  • Alexander

    I definitely have wingmen and am a wingman to a couple friends. In both cases, it looks more like the support role and less like the pragmatic one–that is, they help me think things through and keep me accountable, but don't necessarily 'wing' for me at parties. I'm reminded a bit of the book “The Game.” I don't think there's anything wrong with having friends help direct conversation, but it's not really my style either.

    I think like a lot of things, what a good wingman looks like is different for every guy. But I would bet just about every successful relationship probably has at least one or two good friends' support behind it.

  • e_serrell

    I need a wingman! Or I guess, maybe a wingwoman :) Even when people say they'll be on the lookout for possible guys for me, they never seem to remember… or else they're as bad at meeting guys as I am lol

  • Vanessa_A

    These are very good points, there are “wingwomen” too, sometimes they just need to remember what their role is to help their friend brake the ice. One of the main points to elaborate on is the advice that is being given. Most of the time the person looking in has a better perspective and their advice should be treasured on how they see “Sam and Sally”. I guess that's why it would be better for the wingman or wingwoman to be in a God centered relationship already or have been in plenty of bible study to be able to give the right advice and encouragment.

  • Tom

    Wow, what a concept!
    As I think back about this, I have been a wing man many times. I even was a match maker twice. Once to one of my good and dear CPA buddies, and another with an IRS agent. The first went magnificently, the second, well let's just say, I had to go to tax court to settle our last IRS audit! Make sure that your wing man is a good and dear friend, even a brother or sister. And for crying out loud, be careful with those missiles on the front of those planes in your pictures, Thomas, they look rather inappropriate for courting procedures! ;-)

  • Tom

    I like the John the Baptist analogy. I get a true joy when someone finds God's best. I must decrease and He must increase.

  • observer

    I have read all your archives, and I'm wondering why to continually attack homeschoolers? If I were a homeschooler seeking advice on courtship/dating I would be completely turned off by your treatment of them. Are you really trying to reach them, or are you just going to stand on a soap box to criticize?

  • observer

    I have read all your archives, and I'm wondering why to continually attack homeschoolers? If I were a homeschooler seeking advice on courtship/dating I would be completely turned off by your treatment of them. Are you really trying to reach them, or are you just going to stand on a soap box to criticize?

    • Jason

      I'm an old homeschooler myself, and I don't think Thomas is attacking homeschoolers. To me, he sounds like someone who appreciates the culture but recognizes some of its limitations. You'll notice that he's not attacking courtship, or Godly relationships, or anything like that – he's simply discussing problems that need to be dealt with. I would suggest they're legitimate – my search for answers on these very issues is what brought me to this website!

  • Daniel B

    “To overcome these challenges Sam needs Walter’s help to create opportunities to interact with God fearing single ladies. This may mean throwing parties, sending out text messages to invite people to play ultimate Frisbee or going out to eat after church.”

    As the Walter in this situation, I find this tough to do because the God-fearing single ladies always love to say that this stuff is great idea, they'd love to come, etc, but then don't show up.

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