Why Halloween Can Feel Complicated When You’re Grieving
Halloween is supposed to be fun, right? Costumes. Candy. Carved pumpkins glowing in the dark. A night where you can be anyone—or anything—you want.
But sometimes, it’s… not fun at all.
Sometimes Halloween turns weird when all you can think about is someone who’s dead and how they’re not here to spend it with you. Sometimes it feels stressful AF—especially when the world piles on expectations about how you should be feeling. (“You SHOULD be having a grand old time! You SHOULD be laughing at the haunted house! You SHOULD love dressing up!”)
Maybe you’re in the same room with all those parents who make you think about your own parents. Or maybe the night feels like a performance—smiling, laughing, pretending to love every moment—when inside, you’re just counting down the hours until it’s over.
If this is you, I want you to know: you’re not broken. You’re human. And it’s okay to have conflicting feelings about Halloween.
Why Halloween Can Feel Complicated When You’re Grieving
When you’ve lost someone, the calendar takes on a whole new weight. The first holidays without them become emotional landmarks—moments where absence is louder than anything else. Halloween, with all its playful chaos, might seem harmless compared to more family-centered holidays, but it still carries a punch.
Memories sneak up on you. A certain costume, smell, or song can trigger vivid reminders of them.
The contrast is exhausting. The high-energy, “party” vibe can clash hard with your low emotional reserves.
People expect you to play along. Pretending to be fine can be more draining than simply admitting you’re not.
It’s full of social landmines. Seeing other families together can stir up longing, sadness, or even anger.
And then there’s the pressure—spoken or not—to “get into the spirit.” The truth is, grief doesn’t take a night off for the sake of a holiday.
Why Mixed Emotions Are Normal
From a psychological standpoint, ambivalence—feeling two or more conflicting emotions at once—is not only normal, it’s a sign of emotional complexity. You might genuinely love parts of Halloween (watching your kids trick-or-treat, dressing up, cozy autumn nights, nostalgia from your own childhood) while also feeling deep sadness, anxiety, or loneliness.
Halloween itself has always contained a mix of tones—play and fear, joy and darkness, connection and eeriness. Its roots in the Celtic festival Samhain were about honoring the dead and facing the inevitability of mortality. That complexity is baked in.
Giving Yourself Permission to Feel How You Feel
Here’s the thing: You don’t need to force joy if it’s not there. You don’t need to fake laughter to make others comfortable. And you don’t need to apologize for feeling disconnected from a holiday that everyone else seems to love.
Instead, try:
Setting boundaries. Give yourself permission to skip events that feel too draining.
Creating your own rituals. Light a candle for the person you’re missing. Bake their favorite treat. Wear something that reminds you of them.
Choosing your level of participation. You don’t have to go all in—or all out. Find a middle ground that feels safe.
Letting someone you trust know where your head’s at. It’s easier to step out for a breather when you’ve told someone ahead of time.
You’re Not Alone in This
If you’re struggling with grief during the holidays—Halloween or otherwise—it can feel like you’re the only one. But you’re not. Spaces exist where you can talk about this openly, without judgment or pressure to “cheer up.”
That’s why I host Season’s Grievings, a live holiday grief support group. We meet to navigate the complicated emotions that come with the season, share coping strategies, and create room for the full spectrum of what we’re feeling.
Because whether it’s Halloween, Thanksgiving, or New Year’s Eve—you deserve a place where you don’t have to pretend.
💜 You’re allowed to feel it all.