Enter cuffing season, the unofficial term for the time of year when people seem a little more interested in finding a romantic partner to spend the colder months with.

And honestly? Wanting someone to spend a cozy evening with, make holiday memories with, or simply check in on you after a long day isn’t a bad thing. We’re wired for connection, and there’s something comforting about having people in our lives who make us feel seen and understood.

But I think there’s a more interesting question worth asking this time of year.

Are we making room for the connections we genuinely want, or are we feeling pressure to have them?

Sometimes, those two things can be difficult to separate. We can want a relationship and feel lonely at the same time. We can enjoy dating someone new while also worrying about whether it’s going anywhere. We can love the people in our lives and still wish our relationships felt a little deeper.

From a therapist’s perspective, these are the kinds of feelings worth getting curious about. Not because there’s anything wrong with wanting connection, but because understanding why we’re seeking it can help us make choices that feel more aligned with what we actually need.

So, rather than treating cuffing season as a race to find someone before the holidays, let’s use it as an opportunity to check in with ourselves, take a closer look at our relationships, and consider what meaningful connection might look like for us.

Before You Look for Connection, Get Curious About What It Means to You

When you imagine the relationship you want, what do you picture?

Maybe it’s having someone to cook dinner with, a partner who remembers the little things, or a person you can call when your day has gone completely sideways. Maybe it’s feeling understood without having to explain yourself over and over. Or maybe it’s simply having someone who makes life feel a little less lonely.

Whatever comes to mind, try looking beyond the relationship itself and thinking about how you hope it will make you feel.

There’s a reason this matters. Sometimes, we become so focused on finding a partner that we lose sight of what we’re actually looking for in one. We might pursue someone because they like us, even when we’re unsure whether we like them. We might stay in a situation that doesn’t feel right because starting over sounds exhausting. Or we might mistake the relief of having someone for the deeper experience of feeling connected to them.

This isn’t about overanalyzing every date or questioning every relationship. It’s about giving ourselves permission to be intentional.

If you find yourself wanting a relationship more intensely as the holidays approach, try sitting with a few questions:

• What am I craving most right now: companionship, affection, emotional safety, validation, stability, or something else?
• What do I hope a relationship will add to my life?
• Am I excited about the possibility of getting to know someone, or am I mostly worried about being alone?
• What helps me feel safe, respected, and understood in a relationship?

You don’t have to journal for an hour or arrive at some life-changing realization. Even a few honest minutes can help you recognize what you’re longing for.

And if you discover that part of you is afraid of being single during the holidays, try not to turn that feeling into another reason to criticize yourself. Loneliness is a human experience. Wanting companionship doesn’t mean you’re incomplete, and being single doesn’t mean you’re falling behind.

Sometimes, the first step toward a healthier relationship is understanding what we’re hoping to find in one.

Chemistry Is Exciting. Feeling Connected Is Something Else.

Let’s talk about dating for a moment.

There’s a particular kind of excitement that comes with a new connection. You look forward to their texts, replay conversations in your head, and wonder what might happen next. It’s fun, and it can be a wonderful part of getting to know someone.

But sometimes, the uncertainty can become just as consuming as the connection itself.

When someone is inconsistent, difficult to read, or unclear about what they want, we might find ourselves spending an enormous amount of time trying to figure them out. We analyze their messages, wonder whether we’ve said something wrong, and feel a rush of relief when they finally give us the attention we’ve been waiting for.

That intensity can feel like chemistry, but it doesn’t necessarily tell us whether a relationship is right for us.

A helpful question to ask yourself isn’t just, “Do they like me?” It’s also, “How do I feel in this connection?”

Do you feel comfortable being yourself? Can you express an opinion without worrying that you’ll push them away? Are their actions generally consistent with what they tell you? Do you feel like you’re getting to know a real person, or are you spending most of your time trying to figure out where you stand?

These questions aren’t meant to turn dating into an evaluation. They’re simply reminders that your experience matters, too.

It’s easy to become so focused on being chosen that we forget we’re choosing someone as well.

And if you’re already in a relationship, this same idea applies. Instead of measuring the health of your relationship only by how much you love each other or how long you’ve been together, consider how it feels to actually be in it. Is there room for honesty, mutual effort, and the occasional difficult conversation? Do you feel like you’re growing together, even when things aren’t perfect?

No relationship will meet every need or feel wonderful every day. But there’s a difference between working through normal challenges and consistently feeling that you have to earn someone’s care.

This season, try paying a little less attention to whether a relationship looks right from the outside and a little more attention to how it feels on the inside.

Sometimes, Connection Starts With Saying What We Need

One of the things that can make relationships so complicated is that we all have different ideas about what connection looks like.

Maybe you feel loved when someone checks in throughout the day, while your partner tends to show love by taking care of practical things. Maybe you need a little reassurance after an argument, while the other person needs some quiet time before talking. Neither person necessarily has bad intentions, but both can end up feeling misunderstood.

And sometimes, instead of explaining what we need, we hope the other person will figure it out.

We say, “You never make time for me,” when what we really mean is, “I’ve been missing you, and I want to feel like spending time together matters to you.”

We say, “You don’t listen,” when we’re really hoping someone will slow down, put their phone away, and try to understand what we’re saying before offering a solution.

It’s understandable. Expressing a need can feel vulnerable, especially if we’ve experienced rejection or disappointment in the past. It can feel safer to express frustration than to admit that we’re hurt or that something matters to us.

But the people in our lives can’t always understand what we need unless we give them a chance to hear it.

The next time you feel frustrated with someone, pause for a moment and ask yourself: What am I actually wanting from this interaction?

Are you looking for reassurance? More time together? An apology? A chance to explain yourself without being interrupted?

Once you have a better sense of what you need, try putting it into words.

Instead of saying, “You never make time for me,” you might say, “I’ve been missing spending time together. Could we plan an evening this week when we can really focus on each other?”

Instead of saying, “You should know why I’m upset,” you could try, “I’m having a hard time explaining why this hurt me, but I want to talk about it. Can we work through it together?”

The goal isn’t to find the perfect words or guarantee that the other person will respond the way you hope. It’s to create an opportunity for understanding.

And remember, communication is a two-way street. You can learn to express your needs clearly, but you cannot make another person listen, respond with care, or take responsibility for their part in a relationship. Their response gives you important information, too.

What If We Treated Connection Like Something We Practice?

We often think about relationships in terms of big moments: the first date, the anniversary, the difficult conversation, or the decision to take the next step.

But much of what makes a relationship feel meaningful happens in the moments between those milestones.

It’s asking a follow-up question when someone tells you about their day. It’s remembering something a friend was worried about and checking in later. It’s noticing when your partner is overwhelmed and asking what would help. It’s putting your phone down when someone is trying to tell you something important.

The Gottman Institute describes small attempts to connect as bids for connection. These are the everyday ways people reach for attention, affection, interest, or support. Responding to those moments can help build a stronger sense of emotional connection over time.

You can explore more about this approach through the Gottman Institute’s relationship resources.

I like this idea because it takes some of the pressure off. We don’t have to plan an elaborate date or have a profound conversation every week to nurture our relationships. We can start with the little things.

Over the next week, try choosing one small way to connect with someone each day.

Maybe you reach out to a friend you haven’t talked to in a while. Maybe you tell your partner something specific you appreciate about them. Maybe you ask someone how they’re really doing and give them enough space to answer honestly.

You could even try a simple ten-minute check-in with someone you care about. Put your phones away, ask each other what’s been on your minds, and focus on listening rather than fixing.

Pay attention to what happens. Which moments feel natural? When do you notice yourself becoming distracted or uncomfortable? What helps you feel closer to someone?

And if you’re single, don’t wait until you’re in a relationship to practice these habits. Friendships, family relationships, and community can all provide meaningful opportunities for connection.

Romantic love can be a beautiful part of life, but it isn’t the only place we get to experience belonging.

Making Room for Boundaries, Especially During the Holidays

Of course, getting closer to people doesn’t mean saying yes to everything they want from us.

The holidays can bring a particular kind of relationship pressure. Maybe your family wants to know when you’re getting married. Maybe you’re navigating whether to introduce a new partner to your relatives. Maybe you feel obligated to attend every gathering, even when you’re already exhausted.

And sometimes, the desire to keep everyone happy can leave very little room for what you actually want.

This is where boundaries become important.

A boundary isn’t about controlling another person’s behavior. It’s about recognizing your own needs, identifying what you’re comfortable with, and deciding how you’ll respond when something doesn’t work for you.

For example, if you’re tired of answering questions about your relationship status, you might say, “I’m happy to share what’s going on in my life when there’s something I want to share, but I’d rather not make my relationship status the focus of the holiday.”

If you’re feeling overwhelmed by social plans, you could tell your partner, “I want to spend time with everyone, but I also need some downtime. Can we look at the schedule together and decide what feels manageable?”

And if a conversation becomes too heated, you might say, “I care about working through this, but I’m getting overwhelmed. I need a little time to regroup, and I’d like to come back to it when I can be more present.”

The words themselves matter less than the intention behind them. You’re acknowledging that your needs deserve consideration, too.

Someone might still be disappointed. They might not understand your decision immediately. Setting a boundary doesn’t guarantee that everyone will agree with you, and it doesn’t mean you don’t care about their feelings.

It simply means their feelings aren’t the only ones that matter.

If you find boundaries particularly difficult, consider exploring Love Is Respect, which offers educational resources about healthy relationships, respect, and boundaries in dating.

You can also use these ideas as a starting point for reflecting on the relationships in your own life. Where do you feel comfortable being yourself? Where do you find yourself agreeing to things you don’t want? What might change if you trusted that your needs were worth expressing?

You don’t have to answer all of those questions today. Sometimes, simply noticing a pattern is a meaningful place to begin.

A Little Relationship Reset for the Season Ahead

By now, you might be thinking about a conversation you’ve been avoiding, a pattern you recognize, or a relationship you’d like to nurture a little more intentionally.

Before moving on, take a moment to check in with yourself.

Imagine that you’re sitting down with your notebook, a warm drink, and a few minutes of quiet. There’s no need to fix anything or make a big decision. You’re simply giving yourself a chance to reflect.

Try finishing these sentences:

• Lately, I’ve been craving more…
• I feel most connected to others when…
• One pattern I notice in my relationships is…
• Something I wish I felt more comfortable communicating is…
• One small thing I can do to nurture a meaningful connection this week is…

Choose whichever prompt stands out to you. Write a few sentences, or just sit with the question for a moment.

As you reflect, try to approach yourself with the same curiosity you’d offer someone you care about. If you notice that you tend to withdraw when you’re hurt, seek reassurance when you’re uncertain, or say yes when you really want to say no, you don’t have to turn that observation into another reason to criticize yourself.

Patterns often develop for understandable reasons. The goal isn’t to label yourself as good or bad at relationships. It’s to understand what you do, what you need, and what you might want to try differently.

If you find yourself returning to the same painful patterns or struggling to work through relationship experiences on your own, a therapist can help you explore those experiences in a supportive setting.

And if you’d like a little more structure for your reflection, that’s exactly why I created the Connection Reset Workbook.

Explore the Connection Reset Workbook on Etsy

This guided resource gives you space to slow down, reflect on your relationships, recognize patterns, and think through practical ways to build more intentional connections. It’s a way to take the ideas you’re exploring here and spend a little more time with them, at your own pace.

You don’t need to have everything figured out before you begin. Sometimes, the most helpful thing we can do is create a little space to ask ourselves better questions.

A Few More Places to Explore

If something in this post resonated with you and you’d like to keep learning, here are a few resources worth bookmarking.

The Gottman Institute: For practical information about communication, emotional connection, and navigating conflict. Explore relationship resources.

Love Is Respect: For information about boundaries, healthy dating relationships, respect, and recognizing unhealthy relationship patterns. Visit Love Is Respect.

Your Therapist’s Notebook: For more reflections and practical tools to support your mental wellness, self-awareness, and relationships. Explore my shop here.

These resources can offer useful starting points, but remember that every relationship has its own context. Educational exercises are not a substitute for individualized support, especially when a relationship involves fear, coercion, or abuse.