“It’s the most wonderful time of the year” … or is it?

For many walking through grief, Christmas doesn’t feel wonderful at all. In this deeply honest episode, Jay reflects on another Christmas without his bride and the complicated, messy reality of holding grief and celebration at the same time.

Drawing from Scripture, personal experience, and the truth of the gospel, Jay explores the difference between seasonal cheer and lasting joy. He reminds us that joy is not the absence of sorrow, but the presence of hope — rooted in belonging to Jesus, the Light of the world.

This episode offers comfort for those who feel lonely, weary, or out of sync with the holiday season, while gently pointing listeners back to Emmanuel — God with us and God for us — even in seasons that don’t feel merry or bright.

If Christmas feels “not so wonderful” this year, you’re not alone. This conversation invites you to choose worship, receive God’s indescribable gift, and trust His goodness as you move forward.

Christmas comes wrapped in lights, music, and cheer, but for those walking through grief, the season can feel completely out of sync with the heart. In this episode, Jay speaks honestly about the tension between cultural “holly jolly” expectations and the real weight of loss, especially when facing Christmas without the one who helped make it meaningful.

Drawing from a personal Christmas Eve journal entry, Jay reflects on how traditions shift, memories surface, and grief deepens during the holidays. Yet he also shares the deeper truth that anchors his heart: Christmas isn’t built on mood, but on Emmanuel—God with us. Even in seasons of grief, God continues to give strength, presence, peace, and hope.

If this Christmas feels different or difficult, this conversation will meet you with honesty, comfort, and the reminder that you don’t have to manufacture joy.

You simply must make room for the One who enters broken places with love.

In this vulnerable and hope-filled episode, Jay shares what it means to steward singleness during the holiday season, a season that carries both beauty and deep complexity for those grieving.

Jay speaks honestly about his own journey as a widower, acknowledging that singleness isn’t something he prefers or celebrates, but a season God has asked him to steward with purpose. With warmth and clarity, he explores how the holidays amplify grief, memories, expectations, and loneliness, yet can still become sacred opportunities to trust God in new ways.

Jay outlines how he is learning to steward his time, emotions, and expectations wisely, while offering practical insight for anyone navigating “different” holidays. He also shares a heartfelt reflection on Christmas without his wife, and how even in broken traditions, the truth of Emmanuel — God with us — remains unshaken.

If you're entering this season with a tender heart, this episode will help you find grace, perspective, and the courage to make room for God in your journey.

Tune in to Episode 47: “Stewarding Singleness During the Holidays.”

Find out more about me here: https://jaycookingham.com

I’m on @buymeacoffee. If you like, even maybe love my podcast, you can buy me a coffee and support me. It’s a simple way of showing your support and helping me grow the podcast. Thank you!

Here’s the link: buymeacoffee.com/jcdude56t

In this heartfelt Thanksgiving episode, Jay shares why gratitude becomes even more meaningful — and more challenging — in seasons of grief. Drawing from Psalm 9:1 and Psalm 28:7, he reflects on the last Thanksgiving his wife spent at home, the pieces of his heart still scattered by loss, and how choosing thankfulness has become a courageous act of trust.

Jay reminds us that gratitude doesn’t erase sorrow; it reframes it. It’s quieter, more tender, and often found in the small, honest moments: the warmth of a coffee cup, the quiet of morning, the unexpected strength to face another day.

Through personal reflection and Scripture, Jay explores how remembering God’s goodness helps us gather the pieces of our hearts again, and how God faithfully meets us in that gathering.

If this Thanksgiving feels heavy or complicated, this episode will help you find one simple, honest thing to thank Him for — and rediscover hope in the middle of brokenness.

Find out more about me here: https://jaycookingham.com

I’m on @buymeacoffee. If you like, even maybe love my podcast, you can buy me a coffee and support me. It’s a simple way of showing your support and helping me grow the podcast. Thank you!

Here’s the link: buymeacoffee.com/jcdude56t

In this episode, Jay dives into a phrase almost every grieving heart knows too well:

“Here we go again.”

That moment when a fresh wave of grief hits, when old wounds reopen, or when the weight of loss resurfaces just when you thought you were finally steady.

Jay explores why grief often repeats itself, why the waves keep coming, and how exhausting it can feel to relive the same emotional ground. He shares candidly about his own struggle with these moments—and the subtle anxiety, self-doubt, and restlessness they bring.

But this episode doesn’t stay in the heaviness.

Jay offers a new perspective: not fighting the wave but learning to ride it back toward God’s presence. He shares a deeply personal prayer that came from a quiet moment with ABBA—an invitation into stillness, surrender, and restoration.

If you’re walking through a season of repetitive waves, this episode will remind you that God meets us in the quiet places we cannot create on our own… and that His goodness remains true even when grief circles back.

Tune in to Episode 45: “Here We Go Again.”

Here’s the prayer I mentioned:

Father,

I give myself over to your quiet.

My quiet isn’t still enough. It’s too loud, too noisy, too busy.

Too much about me.

In your quiet there is peace.

Rescue… rest… restoration.

So, I consecrate my thoughts, emotions, ideas, plans, all that

my mind, heart and soul are consumed with.

I surrender all my agendas, strategies, motivations, attitudes

and my will to you.

I give you all my concerns, worries, doubts, fears and disappointments.

I hold nothing back.

I will be still my King, and I enter your quiet with gratitude.

Thank you for the invitation!

Amen

Find out more about me here: https://jaycookingham.com

I’m on @buymeacoffee. If you like, even maybe love my podcast, you can buy me a coffee and support me. It’s a simple way of showing your support and helping me grow the podcast. Thank you!

Here’s the link: buymeacoffee.com/jcdude56t

What happens when the foundation you’ve built your life on suddenly shifts? In this heartfelt episode, Jay Cookingham opens up about life after loss—about feeling “out of sync,” rebuilding identity, and finding new rhythms when the old anchors are gone.

Jay shares his personal journey through grief, the struggle of comparison, and the healing power of creativity and faith. It’s an honest conversation about re-learning how to live, love, and trust in God’s goodness even in deep sorrow.

If you’re navigating a season of loss or transition, this episode will remind you that hope, grace, and new beginnings are still possible.

Find out more about me here: https://jaycookingham.com

I’m on @buymeacoffee. If you like, even maybe love my podcast, you can buy me a coffee and support me. It’s a simple way of showing your support and helping me grow the podcast. Thank you!

Here’s the link: buymeacoffee.com/jcdude56t

This episode explores what it really means to rediscover joy while still honoring loss. Jay shares about a recent men’s conference that reminded him of how universal grief is and how powerful it can be to talk about it honestly.

As he reflects on nearly six years since Christine’s passing, Jay wrestles with tension, the sacred space where sorrow and joy coexist. Through scripture, stories, and honest confession, he invites listeners to see that grief and joy aren’t opposites, they’re companions.

This episode is about learning to live again, to trust that joy can coexist with sorrow, and to find the courage to keep choosing life, gratitude, and God’s presence, one step at a time.

Find out more about me here: https://jaycookingham.com

I’m on @buymeacoffee. If you like, even maybe love my podcast, you can buy me a coffee and support me. It’s a simple way of showing your support and help me grow the podcast. Thank you!

Here’s the link: buymeacoffee.com/jcdude56t

After 41 episodes of walking through the valleys of grief and glimpses of grace, Jay takes a pause to look back.

In this reflective episode, he unpacks the five recurring themes that have shaped his journey so far: love, God’s relentless goodness, lament, the companionship of joy and sorrow, and trust.

Grief doesn’t stand still, it changes us. It refines, reshapes, and reminds us that even in loss, God continues to give. Through tears and truth, Jay shares what it means to keep moving forward, not away from grief, but deeper into grace.

If you’ve ever wondered whether things can truly change after loss, this episode offers a quiet but powerful yes.

Find out more about me here: https://jaycookingham.com

I’m on @buymeacoffee. If you like, even maybe love my podcast, you can buy me a coffee and support me. It’s a simple way of showing your support and help me grow the podcast. Thank you!

Here’s the link: buymeacoffee.com/jcdude56t