Why Is Dating So Hard? (And Why Being Single Isn’t “Failing” Either)

A gentle guide to why dating feels hard (and why being single can feel complicated too) during the holiday season and how to find joy in both.

The holiday season has a funny way of shining a spotlight on our relationship status, whether we want it to or not.

Suddenly, your social feeds fill with matching pajamas, “first holiday together!” posts, engagement announcements, and family members asking questions you did not agree to be interviewed about.

So if you’ve ever found yourself wondering “Why is dating so hard?” or “Why am I still single?”, just know you’re in good company. This time of year can stir up a mix of excitement, tenderness, loneliness, hopefulness, and the occasional desire to hide in a pantry with a plate of cookies. All of these feelings are valid.

Let’s talk about both sides, dating and being single, and how you can move through this season with more grace, grounding, and joy.

Why Dating Can Feel So Hard During the Holidays

Dating during the holidays can feel…a lot. Especially if it’s a new relationship or you’re still figuring out what you two are.

Here’s the truth: You don’t have to have it all figured out by New Year’s Eve.

Instead of putting pressure on yourself or the relationship, try:

✨ Choosing fun over perfection

The holidays already come with enough pressure, don’t add “create the perfect romantic moment” to the list.

Instead, focus on experiences that feel light, playful, and low-stakes. Go ice skating and laugh when you both inevitably wobble. See a holiday play or concert and let yourselves get swept up in the magic. Wander through a winter market with hot chocolate in hand. Bake cookies together and don’t worry if half of them come out a little uneven.

The point isn’t to impress each other, it’s to enjoy each other. Let fun lead the way, and let connection grow naturally, without forcing it.

✨ Talking about expectations (only if it feels appropriate)

The holiday season can bring up all sorts of unspoken questions, about gifts, how much time you’ll spend together, whether you’re exchanging “Happy Holidays” texts or showing up to family events side by side. These topics can stir up anxiety, especially in newer or undefined relationships.

If it feels right, a simple, honest check-in can take the pressure way down. Something like, “Hey, can we talk about what feels comfortable for us this season?” opens the door without making it heavy. It’s not about planning the next five years, it’s about understanding each other’s expectations so no one feels overwhelmed or surprised.

A little clarity can go a long way in helping both of you relax, let go of holiday relationship pressure and enjoy this time together.

✨ Letting yourself enjoy the moment

You don’t have to know where things are headed to enjoy where you are right now. It’s okay to let yourself lean into the small, good moments: a shared laugh, a cozy night in, a meaningful conversation,without trying to define the entire future in your head.

Dating is hard because it asks for vulnerability, uncertainty, and trust… three things that feel even louder this time of year. The holidays can make you feel like you should have clarity or labels or a grand plan, but you’re allowed to simply be present.

Give yourself permission to enjoy someone’s company without overthinking what it means. Let yourself feel the sweetness of connection without turning it into a high-stakes exam. Be gentle with yourself as you navigate the ups and downs, you’re doing just fine.

Why Being Single Is Especially Emotional During the Holidays

During the holiday, being single (Whether You're Healing, Hoping, or Simply Here) can feel heavy for so many reasons.

Maybe you recently ended a relationship.
Maybe you’re grieving a partner or past relationship.
Maybe dating just hasn’t clicked yet, and the pressure feels louder this time of year.
Or maybe you’re perfectly content with being single but still get asked, “So…seeing anyone?”

No matter what your story is, this season can stir up a lot of holiday loneliness.

Here’s what I want you to remember:

Being single is not a failure. It’s a season. And every season serves a purpose. You’re allowed to feel sad or lonely. You’re allowed to want companionship. And you’re also allowed to find pockets of joy exactly where you are.

Try:

✨ Giving yourself grace

Your worth isn’t tied to your relationship status, and it definitely isn’t measured by whether you bring a plus-one to a holiday dinner. It’s okay to show up as you are: single, newly single, or simply navigating your own path.

This season can stir up expectations from family, friends, or even yourself, but try to treat yourself with the same compassion you’d offer a loved one. Give yourself permission to rest, to set boundaries, and to say no to anything that feels overwhelming.

Being gentle with yourself doesn’t mean you’re giving up, it means you’re honoring your feelings, your pace, and your season of life. You are enough, just as you are.

✨ Having a “joy plan”

The holidays can bring up a mix of emotions: loneliness, pressure, or even just general overwhelm, but you can intentionally create moments that lift your spirits.

Plan a girls’ night filled with cozy holiday fun, festive snacks, and laughter that reminds you how good connection feels. Watch your favorite holiday movie with your favorite person (yes, that can totally be you) and savor every bit of comfort it brings. Treat yourself to something small but meaningful, a candle, a favorite treat, a warm blanket, anything that encourages you to pause and enjoy the moment.

A “joy plan” is about actively crafting experiences that nurture your heart, even when life feels complicated. It’s permission to seek delight and care for yourself, unapologetically.

✨ Giving back in a way that feels meaningful

One of the simplest ways to brighten the holidays, both for yourself and others, is to give in a way that resonates with you. Donate to a food pantry, gift to a family in need, volunteer a few hours if you can, or even perform small acts of kindness in your community.

Helping others often sparks a sense of warmth, connection, and purpose, especially when you might otherwise feel lonely or disconnected. These moments of giving remind us that we’re part of something bigger, and that our presence and care truly matter.

Remember: you’re not behind, you’re not alone, and you’re building toward something, often more meaningful than you realize. Small, intentional acts can create ripples of joy that stretch far beyond the holiday season.

A Gentle Reminder as You Move Toward the New Year

Whether you’re dating, single, or somewhere in between, you deserve love, clarity, comfort, and connection, both with others and with yourself.

Dating is hard because being human is hard.
Relationships are complicated because emotions are complicated.
And being single is not a problem to fix, it’s a chapter to honor.

As the year winds down, try to make room for compassion, for yourself, for others, and for the messy, beautiful, in-progress story you're living.

There is joy available to you in every season. Even this one.

If the holidays, or dating, or being single, are feeling especially heavy this year, know that you don’t have to navigate it alone.

Our therapists are here to support you in finding balance, processing emotions, and discovering joy in whatever season you’re in.

To schedule a session and give yourself the gift of support, understanding, and a safe space to be exactly who you are.

You deserve care, compassion, and connection, especially now.