Episode 139: Wrestling with God through Loss and Disappointment with Tiffany Stein
Episode 139: Wrestling with God through Loss and Disappointment with Tiffany Stein  
Podcast: MESSmerized - Funny and faith based encouragement in marriage , family , Christian parenting , and finding purpose
Published On: Wed Mar 11 2026
Description: Tiffany Stein joins me on the podcast today for a vulnerable and thoughtful conversation about grief, disappointment, and what it looks like to keep wrestling toward God when life falls apart. Tiffany shares the heartbreaking story behind her book Mourning God after losing her infant son, David, and how that loss led her into not only grief over what she had lost, but also grief over the God she thought she knew.Today’s conversation isn’t just for someone who has experienced the death of a loved one. We talk about the many forms loss can take—church hurt, broken relationships, shattered expectations, illness, estrangement, and dreams that never came to be—and how those losses can unravel what we thought we believed about God. Tiffany offers such a wise and honest framework for lamenting for those seasons when God feels silent, prayer feels dry, and faith feels like you’re just barely hanging on.This conversation is deep, hope-filled, and incredibly practical too. Tiffany shares what helped her in the darkest season of her life, how the body of Christ can carry people when they have no strength left, and some genuinely helpful ways to love people who are hurting without resorting to the usual stitched-on-a-pillow responses. If you’ve ever wondered whether God can handle your honest disappointment, or if you’re walking with someone through sorrow and want to love them well, I think this episode will meet you right where you are.All things CynthiaMourning God by Tiffany SteinEvery Moment Holy, Volume II: Death, Grief, & HopeAuthor: Douglas Kaine McKelveyGentle and Lowly: The Heart of Christ for Sinners and Sufferers Author: Dane OrtlundAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy