345: Loving, Practical Ways to Comfort Those Walking Through Grief with Sherrie Pilkington
What does it look like to show up well for those walking through grief? When someone we know is walking through grief, we want to help by knowing what to say to ease their pain.
And yet, many of us feel awkward around grief and loss. We worry that we’ll make things worse by saying the wrong thing. Often we don’t know how to emotionally support others without trying to fix the situation or offer what can feel like empty platitudes.
Today I’ve invited my friend and fellow podcaster Sherrie Pilkington to share her grief journey after the sudden loss of her husband several years ago. As an advocate for those walking through grief, Sherrie offers practical, much-needed suggestions to best care for a loved one on a grief journey in order to show Christian compassion during this challenging time.
WHAT YOU’LL LEARN:
[00:00] Why Grief Feels Confusing and Uncomfortable for Everyone
[09:00] “Grief Doesn’t Need Answers. It Needs…”
[12:00] Why Sitting With Someone’s Grief Is Often More Healing Than Trying to Fix It
[14:00] How Consistent, Thoughtful Support Helps Restore Connection To the Grieving
[16:00] Why Does Being Remembered After the Initial Loss Matter So Deeply?
[18:00] What Does Grief Support Look Like When Words Fall Short?
[23:00] How Simple, Tangible Gifts Can Help Those Grieving Feel Seen
[25:00] Which Phrases Unintentionally Increase Pain for those in Grief?
[29:00] Monthly Grief Boxes: How to Offer Realistic, Specific Help Without Overwhelming the Grieving
[00:00] Why Grief Feels Confusing and Uncomfortable for Everyone
Grief doesn’t move in a straight line, and it rarely looks the way we expect it to, explains Sherrie.
One moment, there may be tears. The next, numbness. Then anger. Then silence. Sometimes all in the same day.
This emotional unpredictability makes grief uncomfortable, not just for the person experiencing it, but for those around them. When pain doesn’t resolve quickly, it can leave friends and family unsure how to respond.
Sherrie shares that this discomfort often leads people to withdraw from those who are grieving, not because they don’t care, but because they don’t know how to stay present with something they can’t fix.
Understanding this helps us reframe awkwardness around the issue of grief. When we know that it’s OK to feel awkward and unable to “fix” the pain a grieving loved one is experiencing, we can offer compassion and care that resonates.
Sudden loss causes life to suddenly be divided into before and after, Sherrie tells us. Routines no longer fit, and the future feels uncertain. Even faith can feel disoriented, not because God has changed, but because the framework for understanding life has.
Because grief reshapes emotional security it can leave the grieving person feeling unsafe in the world, unsure of what can be trusted, and unsure of who they are now.
Sherrie says that recognizing this truth is a great place to start. Grief is not simply sadness, but a full-body, full-life experience that alters how someone moves through the world. Knowing this allows us to better ride the emotional rollercoaster that a grieving person may experience.
Grief can also be difficult because it has a way of stripping away performative faith.
Sherrie shares how grief required a new kind of honesty with God, one that made room for anger, questions, confusion, and pain.
Rather than pushing those emotions away, grief invites them forward. Honest prayer becomes less about saying the “right” words and more about bringing what is real.
This kind of honesty is not a sign of weak faith. It is often a sign of deep trust, the belief that God can hold what we cannot explain.
Grief doesn’t mean God is absent. Often, it’s where His presence becomes most personal.
[09:00] “Grief Doesn’t Need Answers. It Needs..”
Many people feel pressure to do something when someone is grieving.
We reach for explanations, we offer perspective, and we try to bring comfort through words.
But here’s the surprising truth, Sherrie says: Grief doesn’t necessarily need answers.
She describes the importance of simply comforting the grieving person through presence.
Sitting with someone’s pain without rushing, correcting, or redirecting creates emotional safety. It communicates, “You don’t have to manage your grief here.”
This sort of presence gives the grieving person space to be honest with all they’re feeling. Although it may feel like this type of support is insignificant, Sherrie lets us know that it is deeply powerful.
[12:00] Why Sitting With Someone’s Grief Is More Healing Than Trying to Fix It
“There is a portion of grief every person must walk through alone. No one else can remove the loss. No one else can carry the pain away,” Sherrie says.
But what can be shared is the weight of isolation. We can let the other person know that we can’t walk this grief journey for them, but that we can walk beside them as they experience grief’s highs and lows.
After walking the grief journey with many others (including herself), Sherrie says that she’s found that this kind of companionship doesn’t speed healing, but offers a steady, Christ-like foundation to ease suffering.
[14:00] How Consistent, Thoughtful Support Helps Restore Connection to the Grieving
Grief support is often strongest in the early days of loss and then fades. This is normal to human nature as we desire to comfort a grieving loved one, but then we get busy and it seems like time marches on.
Unfortunately, grief doesn’t fade on the same timeline, and this can leave the grieving person feeling abandoned or alone to carry the weight of their emotional pain.
Sherrie speaks to how meaningful support often shows up later: a message months after the loss, remembering important dates, and continuing to reach out when others have moved on.
Consistency communicates remembrance. It says, “You still matter. Your loss still matters.”
This kind of care restores connection in a season when grief can feel deeply isolating.
[16:00] Why Does Being Remembered After the Initial Loss Matter So Deeply?
Being remembered helps tether a grieving heart to the world outside of pain, Sherrie explains.
“When someone reaches out long after the initial wave of support has passed, it interrupts the sense of invisibility that often settles in,” she shares.
Small gestures such as a note, a gift or a message can gently remind someone they are still seen, still held and still part of a community.
[18:00] What Does Grief Support Look Like When Words Fall Short?
When words feel inadequate, actions become especially meaningful to the grieving.
Practical comfort often looks simple: meals, notes, sitting quietly and small acts of care. These gestures reduce the emotional and logistical burden grief brings.
They don’t take pain away, but they soften the environment around it and give the grieving person space to be seen in their pain.
[23:00] How Simple, Tangible Gifts Can Help Those Grieving Feel Seen
Sherrie shares how thoughtful, physical reminders of care can speak kindness and love when conversation feels exhausting. Items that engage the senses, invite reflection, or simply say “you are remembered” can be deeply grounding, she explains.
This is the heart behind her grief-focused subscription boxes (Sealed with a Hug) created to offer ongoing, gentle reminders of presence and care rather than one-time gestures that quickly fade.
Grief doesn’t end when the funeral does. Consistent, tangible support acknowledges that reality, she tells us, and that’s why she’s created this service to help others love the grieving well .
[25:00] Which Phrases Unintentionally Increase Pain for Those in Grief?
Sherrie shares that statements that attempt to explain loss, minimize pain, or rush hope can leave the grieving person feeling misunderstood or pressured to heal.
Consider how language matters and how listening often comforts more than speaking, she says.
Sherrie says that open-ended offers like “let me know if you need anything,” often place emotional labor back on the grieving and can feel empty.
She suggests specific, gentle offers because they remove the need for the grieving person to decide, ask, or explain.
[29:00] Monthly Grief Boxes: How to Offer Realistic, Specific Help Without Overwhelming the Grieving
Support is most helpful (for both the griever and the person loving them through their journey) when it is manageable and consistent.
She encourages offering what you can realistically give, especially if you can offer it on an ongoing basis as this creates trust. Small, repeated acts often carry more weight than grand gestures and can mean the world to a grieving person.
Also, it’s important to note that grief is not limited to death, but that loss can come through various forms, including health, relationships, identity, and unmet expectations.
Finally, Sherrie reminds us that grief is not meant to be carried alone.
She envisions the potential for the grieving to be supported in multiple ways, such as church families and loved ones that create space for sorrow without rushing it.
Connect with Sherrie Pilkington via her podcast Finding God in Our Pain, on Instagram (@livelovedthrive), or check out her Sealed With a Hug Grief Boxes (for those wanting to support others walking through grief).
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RELATED EPISODES:
Ep 119 — Find Healing Through Grief by Serving Others with Ashley from Bridget’s Cradle
Ep 177 — Coping with Grief and Shattering Loss When Tragedy Strikes (with Lisa Appelo)
Ep 297: Believing in God’s Love Again After You’ve Been Hurt with Rachael Adams
