Loneliness and Connection: Learning When to Let Go

Break Free with Ashley Winston

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Friendship is one of life’s greatest gifts—but it can also be one of our biggest struggles when we approach it from a place of emptiness. In this episode of The Break Free Podcast, Ashley offers a raw and honest conversation on what it really takes to build healthy, God-centered friendships.

She challenges the tendency to make people our source, reminding us that true fulfillment only comes from God. When we skip that step, we set ourselves up for disappointment—overinvesting, ignoring red flags, or clinging to relationships that have already expired. Instead, Ashley shows us how to first cultivate self-connection and wholeness in Christ so that our friendships are not rooted in lack, but in abundance.

With her signature mix of biblical wisdom and practical truth, Ashley breaks down the importance of discernment, capacity, and courage in our relationships. She explains why mismatched capacity leaves us drained, why loneliness is not a curse but a call to preparation, and how to identify the people who are truly equipped to walk with us in our purpose.

This is more than a message about friendship—it’s an invitation to realign your circle, release what no longer fits, and step into the kind of authentic, sharpening relationships God designed for you to thrive in.

Visit the link in Ashley’s Instagram bio @theashleywinston to sign up for her email list and stay connected for weekly insights, mentorship opportunities, and more transformative content.

73 episodes

#Religion #Ashley Winston