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Guide to Being a Great Wingman

Apr 30, 2025

How to Be a Wingman or Wingwoman

Introduction

  • The role of a wingman is to make your buddy look cool and attractive.
  • Think of a wingman like George Clooney in Ocean's Eleven.
  • Be inclusive of both wingmen and wingwomen.

Key Steps to Being a Wingman

Step 1: Point Out the Target

  • Identify the person your friend is interested in.
    • "Call your shot" like Babe Ruth.
    • Ensure the wingman knows who not to make a move on.

Step 2: Call the Play

  • As a wingman, act like the head coach.
  • Have a plan rather than just saying what's on your mind.
  • Example plan:
    • One person approaches while the wingman waits.
    • Wingman joins when signaled.

Step 3: Introduce the Wingman

  • Avoid formal introductions like "Girls, I'd like you to meet..."
  • Introduce your friend to the girls informally.

Wingman Don’ts

  • Don't talk about sensitive topics: Refrain from talking about your friend's anatomy.
  • Don't lie: Avoid inventing false stories or exaggerations.
  • This isn't third grade: Don't relay childish messages like "my friend thinks you're cute."

Important Reminders

  • Engage the Friends: Make sure the friends are having a good time to avoid sabotaging the situation.
  • Slow Exit: Gradually distance yourself to let your friend take over if things go well.

Final Thoughts

  • If it doesn't work out, it's not the end - the speaker is not a pickup artist.
  • Approach is often casual, involving humor and improvisation.

Additional Content

  • Mention of a podcast "The Basement," available on YouTube, iTunes, and SoundCloud.
  • Discussion of songs that evoke emotions, such as "Landslide."
  • Reference to movies like "Jack Frost" and their emotional impact.