Navigating Holiday Disappointment When Things Don’t Go as Planned

The holidays carry a lot of hope, don’t they?

We imagine meaningful moments, cozy gatherings, smooth travel, cheerful kids, peaceful family time… and then reality arrives with its own agenda.

Plans shift.

Family dynamics flare.

Someone gets sick.

Travel falls apart.

The day feels rushed instead of restful.

Or the moment you were counting on simply… doesn’t happen.

Navigating holiday disappointment is incredibly common. Yet most people don’t talk about it because it can feel “ungrateful” to acknowledge how things fell short. But naming disappointment isn’t negativity — it’s honesty. And honesty is often the first step toward staying connected when things don’t go the way you hoped.

Let’s explore how to navigate holiday disappointment with care, compassion, and connection.

Start by Naming the Real Feeling Beneath the Disappointment

Disappointment is often a headline emotion. Underneath it lives something far more vulnerable and therefore far more important to understand.

Usually, it’s something like:

• Hurt — “I wanted to feel included.”

• Longing — “I hoped for something special between us.”

• Grief — “This holiday isn’t the way it used to be.”

• Overwhelm — “I didn’t realize how much I needed rest.”

• Frustration — “We tried so hard, and it still didn’t work out.”

When you identify the underlying feeling, you’re better able to express what you need. It also helps your partner understand you rather than guess.

Try a gentle reframing:

Instead of:“That didn’t go how I wanted.”

Try:“I’m feeling a little sad because I’d really been looking forward to ___.”

This shift turns a statement of dissatisfaction into an invitation for connection.

Avoid the Spiral of Comparison

Holiday disappointment can intensify when we compare our experience to:

• Curated social media posts

• “Perfect” memories from childhood

• Holiday traditions that feel impossible to recreate

• The version of the holiday we imagined in our heads

This comparison creates a gap between expectation and reality. Know that disappointment grows in that gap.

So, if you notice your thoughts drifting toward “should,” gently call it out:

“I think I’m comparing again. Let me take a breath.”

This brings you back into the present moment, rather than the imagined one you feel you’ve failed to create.

Talk With Your Partner, Not at Them

When holidays go off-script, it’s easy for couples to fall into blame or criticism, especially of one another:

“You didn’t help enough.” “Your family stresses me out.” “We should have planned better.”

It happens to the best of us! So let me gently remind you of this very important fact: disappointment doesn’t need a villain. And assigning one only leads to defensiveness.

So, instead, try a softened start-up or healthy conflict-resolution strategies. This might look or sound like:

“I’m feeling disappointed, and I’d love to talk about it with you so we can feel more connected.”

In doing this, you open space for teamwork rather than tension.

Give Each Other the Benefit of the Doubt

Holidays often activate tender emotional places, including nostalgia, old wounds, family expectations, pressure to “make it special,” and grief about what’s changed. Your partner might be carrying their own disappointment, even if they’re not saying it.

Practice what Dr. Becky calls the Most Generous Interpretation.

Assume your partner is doing the best they can with the emotional and mental load they’re carrying.

This mindset helps shift from frustration to compassion.

Compassion doesn’t erase disappointment, but it softens the edges enough to allow reconnection.

Look for the Micro-Moments That Did Go Well

Even during stressful or messy holidays, micro-moments of connection almost always appear, like a:

• Shared laugh.

• Moment of teamwork.

• Grounding hug.

• Joyful reaction from a child.

• Glance that says “we’re in this together.”

• Quiet exhale at the end of the night.

These moments help remind you that connection isn’t built on grand plans. They’re built on small, meaningful interactions.

Try asking each other:

“What’s one small thing from this holiday that felt good?”

You’re not invalidating disappointment. You’re widening the lens so the disappointment doesn’t become the entire story.

Adjust Next Year’s Plans From a Place of Collaboration, Not Reaction

Once emotions have settled, revisit the holiday with curiosity rather than criticism:

• What worked well?

• What felt stressful or draining?

• What would you like to do differently next time?

• Did any boundaries feel helpful?

• Were any missing?

• What brought you joy, even in small ways?

This reflective conversation transforms disappointment into insight rather than resentment.

The goal isn’t to engineer a flawless holiday; it’s to create a holiday that aligns with your needs, values, and emotional bandwidth as a couple.

Give Yourself Permission to Grieve the Holiday You Imagined

Sometimes disappointment lingers because we’re fighting the feeling. We tell ourselves:

“I shouldn’t be upset.”“It wasn’t a big deal.”“Other people have it worse.”

But emotions don’t disappear because we decide they’re inconvenient.

You’re allowed to feel:

• Sad

• Let down

• Overwhelmed

• Lonely

• Frustrated

• Or simply… tired

These feelings don’t make you ungrateful.

They make you human.

Grieving the holiday you hoped for is often what allows you to fully return to the holiday you actually had.

Final Thoughts on Navigating Holiday Disappointment

Holidays rarely go exactly as planned for any of us, despite the shiny Instagram photos or joyful videos we choose to share with the world!

But navigating holiday disappointment doesn’t have to create distance between you and your partner this holiday season.

With honesty, empathy, thoughtful boundaries, and curiosity about each other’s inner worlds, you can navigate the messy parts of the season together and come out feeling more connected.