Navigating the Holidays When Grief, Family, and Loneliness Share the Table
by Jessica Anne Pressler, LCSW
If you are reading this with a tight feeling in your chest as the holidays approach, you are not alone, and there is nothing wrong with you.
From Thanksgiving through Christmas, Hanukkah, Kwanzaa, and New Year’s, the holiday season is often portrayed as a time of gratitude, family, joy, and togetherness. We see warm kitchens, glowing lights, overflowing tables, and generations laughing together. But for so many people, the holidays bring a far more tender and complicated mix of emotions. There may be grief for someone who is no longer at the table. There may be tension with family, quiet loneliness, or the exhausting effort of appearing happy while you are hurting inside.
For some, there is a literal empty chair. For others, the empty chair is symbolic, a reminder of everything that has changed. Whether through death, divorce, estrangement, or the slow loss of a relationship as it once was, that chair can hold an enormous amount of love and sorrow.
If this is your holiday season, please be gentle with yourself. You are not ungrateful. You are not broken. You are not doing the holidays wrong. You are a human being carrying something heavy into a season that often pretends no one is.
The Empty Chair: Navigating Grief When Someone Is Missing from the Table
The holidays have a way of making grief feel brand new. A loss that has softened over the months, even years, can rise up all at once when you set the table and realize you need one fewer plate, or when you open the box of ornaments and find the one they always hung. The holidays are built on rituals, and rituals are built on people: the person who always carved the turkey, who baked the cookies just the way you loved them, who lit the candles, who told the same story every year, who called first thing in the morning to wish you a happy holiday. When that person is gone, the ritual itself can feel like an echo of their absence.
If the tears come unexpectedly this season, in the grocery store aisle, when a familiar song plays, while wrapping gifts, or in the middle of a conversation, please know that this is not weakness. It is normal.
You do not have to choose between honoring your loss and being present for the season. You can hold both, in whatever way feels right for you. Here are some gentle ways to keep your loved one close:
• Set a place for them at the table, light a candle in their honor, or place a cherished photograph nearby.
• Make their signature dish, hang their favorite ornament, and invite others to share a favorite memory.
• Write them a letter telling them what you wish they knew and keep it close throughout the season.
• Give yourself permission to step outside for fresh air or a quiet moment alone whenever the waves of grief rise.
• Allow yourself to laugh, too. Joy is not a betrayal of the person you miss.
• There is no right way to spend the holidays. Some people find comfort in keeping every tradition exactly the same. Others need to change everything because the old ways hurt too much. Both are completely valid. Listen to your heart and honor what you need this year, knowing that your needs may be different next year, and that is okay too.
Why the Holidays Can Make You Feel Worse, Even When You Are Supposed to Feel Joyful
Our culture sends a clear and constant message about this season: be grateful, be merry, be with family, be happy. When what you feel inside doesn’t match that picture, it is so easy to believe that something is wrong with you. Many people quietly layer guilt on top of their sadness, telling themselves, “I have so much to be thankful for. Why can’t I just enjoy this?”
If you have asked yourself that question, I want to offer you some kindness. Sadness and gratitude are not opposites. They can live side by side in the same heart. You can be thankful for your health and still ache for your mother. You can treasure your friends and still grieve the family you wish you had.
Cultural expectations around gratitude, family, and happiness can leave people feeling ashamed of their loneliness and complicated emotions, when in truth those feelings are a natural, deeply human response to loss and disappointment. Often, the guilt hurts more than the sadness itself. When you release the expectation that you should feel a certain way, you may discover a quiet relief, the relief of simply being allowed to feel what you feel.
Grieving Someone Who Is Still Alive
Not every empty chair belongs to someone who has died. Sometimes the empty chair represents an estranged parent, a sibling you no longer speak with, an adult child who has pulled away, or a former spouse whose absence still reshapes the family. This kind of loss can be especially painful during the holidays, in part because it is so rarely acknowledged.
This is sometimes called ambiguous loss: grieving a person who is still here or grieving the relationship you longed for and never fully had. There may be no funeral, no sympathy cards, no casseroles left on the doorstep. Others may not understand, and some may even urge you to reconcile “for the sake of the holidays.” If you chose distance to protect yourself, you may feel relief and sorrow at the very same time. Please know that both feelings are allowed. Choosing to protect your heart does not necessarily mean you stopped loving. I may just mean you love yourself enough to protect your emotional wellbeing.
If you are carrying this kind of grief, here are some ways to care for yourself:
• Name it as grief. Giving your pain its true name allows you to offer yourself the compassion you would offer anyone in mourning.
• Gently remind yourself why the distance exists. Holiday nostalgia can blur the very real reasons behind a difficult decision.
• Allow yourself to grieve the relationship you hoped for, not only the one you had.
• Reach out to at least one person who truly understands, whether a trusted friend, a therapist, or a support group, so you do not have to hold this alone.
Setting Boundaries During the Holidays Without Feeling Guilty
For many people, the hardest part of the holidays is not the cooking, the shopping, or the travel. It is bracing for the intrusive questions, the uncomfortable conversations, the unwanted visits, and the unspoken expectation that you will quietly set aside your own needs so everyone else can stay comfortable.
I want you to hear this clearly: your well-being matters too. Boundaries are not walls built to punish others. They are gentle fences that protect your heart and help preserve the relationships you can truly sustain.
Here are some caring ways to protect yourself this holiday season:
• Decide ahead of time how long you will stay at each gathering and plan your own transportation so you can leave when your heart tells you it’s time.
• Prepare a few simple phrases for intrusive questions, such as “I’d rather not talk about that today,” or “That’s something I’m keeping private for now.” You do not owe anyone an explanation.
• Redirect the conversation with warmth: “Let’s talk about something happier. Tell me about your new job.”
• Remember that it is okay to say no to hosting, to visits, to certain events, or to a gathering altogether.
• Ask a trusted friend to check in with you before, during, or after a difficult gathering. Even a simple text can feel like a hand to hold.
• Listen to your body. If your chest tightens or your stomach drops, that is your body speaking to you. Stepping outside or taking a few quiet minutes alone is always allowed.
If guilt shows up when you set a boundary, please be patient with yourself. This is especially common if you grew up believing your needs came last. Feeling guilty does not mean you have done something wrong. Often, it simply means you are doing something new, and new things take time to feel safe.
Why Family Gatherings Can Bring You Right Back to Childhood
Many adults who have spent years lovingly tending to their own healing are surprised by how quickly they feel small again the moment they walk through their family’s front door. Old family roles, unresolved wounds, and familiar patterns can resurface around the holiday table almost instantly.
The peacemaker begins quietly managing everyone’s moods. The one who was always criticized starts bracing for the next remark. The “good child” slips back into performing. Suddenly you are not the capable, grounded adult you are the rest of the year. You may feel like a frightened eight-year-old, scanning the room to keep everyone calm.
If this happens to you, please don’t be hard on yourself. Your nervous system remembers. The sights, sounds, smells, and voices of childhood, and the holiday traditions woven through them, can awaken the very same protective responses you developed long ago, when you needed them most. Being pulled back into old patterns is not a sign that your healing has failed. It is a sign that you are noticing, and noticing is where every meaningful change begins. Please gently remind yourself: I am an adult now. I am safe. I have choices. I no longer need my “Traitor Within.”
When the Holidays Become an Exercise in Self-Abandonment
Some people spend the entire holiday season taking care of everyone else’s feelings. They avoid conflict at all costs, smooth over every tense moment, and pretend everything is fine, even when it isn’t. By the time the season ends they feel drained and hollow, and they may not even understand why.
If this sounds familiar, please know that this pattern did not come from nowhere, and it is not a character flaw. I describe it through the lens of the Traitor Within. The Traitor Within is a misguided, well-intentioned aspect of self that repeatedly leads us down self-destructive pathways. The traitor is primarily formed in childhood as adaptive responses to trauma and dysfunction, in order to feel safe, shaped by the messaging and modeling of those around the child. It originally served a protective function. These patterns persist into adulthood as an inner monologue or state of being that drives repetitive self-defeating behavior, transforming what was once survival into self-sabotage.
At the holiday table, the traitor might whisper, “Just stay quiet. Don’t ruin the holiday. It’s only one day.” That voice once helped you survive, and it deserves your understanding. But today, it may be keeping you small. You can thank it for trying to protect you and still choose differently.
Breaking free of this pattern begins with gentle awareness:
• Notice the moment you begin to set aside your own feelings to keep the peace and meet that moment with kindness rather than criticism.
• Ask yourself softly, “What do I truly need right now?” and honor even one small answer.
• Remember that other people’s emotions belong to them. It was never your job to hold the whole family together.
• Offer compassion to the part of you that is trying to protect you, while giving yourself permission to respond in a new way.
When Gratitude and Holiday Cheer Become Toxic Positivity
Gratitude can be a beautiful, healing practice, and holiday cheer can be a genuine gift. But when either is used to quiet someone’s pain, it becomes toxic positivity. “At least you have your health.” “Look on the bright side.” “Cheer up, it’s the holidays.” These words are often well-intended, yet they can leave a grieving heart feeling unseen and alone.
Being thankful for what you have does not mean you cannot grieve what you have lost. It does not mean you cannot feel disappointed by your family or admit that this season is genuinely hard. True gratitude has room for honesty. In fact, gratitude often feels most authentic when we stop forcing it and allow all our feelings to sit together at the table. You are allowed to say, “I am grateful, and I am hurting,” all in the same breath.
Why We Romanticize Family During the Holidays
Nostalgia is powerful. Childhood traditions, holiday movies, familiar carols, and the cultural image of the perfect family can lead us to remember the warmth and forget the wounds. During the holidays, it is so common to find ourselves minimizing harmful dynamics, telling ourselves, “it wasn’t that bad,” or returning to relationships that consistently leave us emotionally depleted.
It is natural to long for the family we wish we had. That longing is tender and deserves your compassion, not your judgment. And yet, longing is not the same as reality. Before the holidays, it may help to gently ask yourself: How do I usually feel after these gatherings? What actually happens, rather than what I hope will happen? Holding onto your truth is not bitterness. It is a quiet act of self-respect and self-care.
How Lonely the Holidays Can Be
For those who are single, recently divorced, widowed, far from home, or estranged from family, the holidays can be the loneliest time of the year. Feeling alone can be especially painful when you are surrounded by images of happy families and couples celebrating together. Social media fills with photographs of crowded tables, matching pajamas, and midnight kisses, and it can feel as though everyone belongs somewhere except you.
If you are spending the holidays alone, I want you to know that your loneliness is not a personal failure, and it says nothing about your worth. Loneliness is simply a sign that we are wired for connection. It deserves tenderness, not shame. Here are some gentle ways to care for yourself during a lonely season:
• Take breaks from social media. Remember that photographs capture a single moment, never the whole story.
• Create small rituals that are entirely yours: a walk by the ocean, a favorite comfort meal, a cozy movie, or a warm bath.
• Reach out to someone else who may be alone. Connection often begins with one kind text.
• Look for a Friendsgiving, a community holiday dinner, a gathering of friends, or a meaningful way to volunteer.
• Plan something to look forward to after each holiday, so the hardest days feel like moments to move through rather than endless stretches.
Being single during the holidays does not mean you are unloved or incomplete. Your life is not on hold until someone fills a chair. You are whole, exactly as you are.
Getting Through the Holidays After Loss
Whatever your empty chair represents, the goal this year does not have to be a perfect holiday season. The goal can simply be to get through it with as much kindness toward yourself as you can offer. As you prepare, here are a few loving reminders:
• Lower your expectations. Good enough is truly enough.
• Plan ahead and also give yourself permission to change your plans at the very last minute.
• Let yourself feel whatever comes, without judging it.
• Rest whenever you can. Grief and family stress are exhausting, both emotionally and physically.
• Reach out for support if the season feels overwhelming. You were never meant to carry this alone.
The empty chair may feel heavy this holiday season. You may cry, laugh, feel numb, or feel all of it within the same hour. Whatever you feel is okay. Gratitude and grief can share the same table, and so can sorrow and hope.
However, you spend these days, please remember that you deserve compassion, especially from yourself. Speak to yourself the way you would speak to someone you love who is hurting. Wrap yourself in the same tenderness you so freely offer others. Your heart matters. And you are not alone.
About the Author: Jessica Anne Pressler, LCSW, is a licensed clinical social worker who has been a psychotherapist for nearly 40 years. She developed the "Traitor Within" framework to help people name and understand the repetitive self-sabotage that shows up in their adult lives. She is the host of the podcast Your Traitor Within, author of Your Traitor Within: A Year of Journaling Prompts for Healing and Empowerment, and author of her debut novel, Traitor Within — How Her Fear of Abandonment Led Her to Abandon Herself. To learn more go to jessicaannepressler@gmail.com
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