Slightly Unsupervised

Same Friendship, Different Rules: Why Generations Don’t Get Each Other


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Same Friendship, Different Rules: Why Generations Don’t Get Each Other 

Ever feel like you and someone you care about are speaking completely different emotional languages?

You’re not imagining it… it might be generational.

In this episode of Slightly Unsupervised, Jennifer and Jackie dive into why friendships across different generations can feel confusing, frustrating, and sometimes even hurtful—even when both people genuinely care.

From communication styles and emotional expression to boundaries, loyalty, and expectations, every generation was shaped differently… and those differences don’t just disappear in friendships.

Jennifer and Jackie get real about:

  •  Why generational clashes happen (and why it’s not always personal) 
  •  The biggest friction points between Gen X, Millennials, and Gen Z 
  •  How the way you were raised shapes how you show up as a friend 
  •  Real-life examples of generational misunderstandings in families and friendships 
  •  Why some people want to talk everything out… and others just want you to move on 
  •  How to navigate friendships when you see the world completely differently 

They also share honest stories about family dynamics, different perspectives, and the challenge of trying to connect when your emotional wiring doesn’t match.

Because sometimes…
 👉 it’s not the friendship that’s broken

…it’s the framework you’re both using.

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Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.

This episode of Slightly Unsupervised was brought to you by the creators of Bestiemony®—the original friendship ceremony that proves soulmates don’t always come with a marriage license. Hosted by Jennifer and Jackie: best friends, business partners, and co-founders of the movement celebrating real, ride-or-die love.

💍 Book a Bestiemony: rhinestoneweddingchapel.com/bestiemony
📱 Follow us on Instagram at @Bestiemonies
📩 Got a bestie story to share or a subject request? Email us at [email protected]

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Slightly UnsupervisedBy Jennifer Hobbs & Jackie Schroeder