Medium

Caleb Dempsey

he/him

Pinned

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Prism & Pen

by

Caleb Dempsey

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Jan 16

The Shape of Loving a Straight Man

It’s Not Always Brokeback Mountain — Sometimes It’s Just Awkward as Hell

The Shape of Loving a Straight Man

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Black Bear

by

Caleb Dempsey

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Nov 11, 2025

Hyper-Independence: The Trauma Response We Keep Calling Strength

How self-reliance can hide fear of being let down, and what healing really looks like.

Hyper-Independence: The Trauma Response We Keep Calling Strength

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Prism & Pen

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Caleb Dempsey

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Nov 11, 2025

The Queer Art of Feeling Safe

What love teaches you after a lifetime of scanning for danger

The Queer Art of Feeling Safe

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Never Stop Writing

by

Caleb Dempsey

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Oct 22, 2025

I Went Looking for Healing and Found a Funnel Instead

How spirituality, sales, and psychology collide in the modern wellness industry.

I Went Looking for Healing and Found a Funnel Instead

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Prism & Pen

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Caleb Dempsey

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Aug 8, 2025

A Gay Son’s Guide to Healing from Family Shame

Because being gay was never the problem. Their shame was.

A Gay Son’s Guide to Healing from Family Shame

In

Never Stop Writing

by

Caleb Dempsey

·

Jun 12

When Compassion Is Used to Avoid Accountability

How spiritual softness becomes image management instead of genuine connection

When Compassion Is Used to Avoid Accountability

In

Never Stop Writing

by

Caleb Dempsey

·

May 31

The Habit of Almost Changing My Life

I thought insight would fix me. It didn’t.

The Habit of Almost Changing My Life

Caleb Dempsey

·

May 29

Introducing: The Tender Deflection Series

How Spiritual Softness Becomes a Shield — And Why Naming It Matters

Introducing: The Tender Deflection Series

In

Never Stop Writing

by

Caleb Dempsey

·

Jan 15

When Ceremony Becomes Aesthetic

How “Ceremonial” Cacao Became a Wellness Performance

When Ceremony Becomes Aesthetic

Caleb Dempsey

·

Jan 15

When Vulnerability Is Turned Into a Product

How spirituality, sales, and psychology collide in the modern wellness industry.

When Vulnerability Is Turned Into a Product

Caleb Dempsey

Caleb Dempsey

he/him

Writing through the soft ache of becoming. Queer. Curious. Quietly unlearning. Lets Connect: AwakeExpress@friendlygeek.com.au

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