How to Date Your Art

Painting By Eric Wieringa

I’ve been thinking a lot about relationships lately. About how our romantic relationships often mirror the way we relate to our art.

Some people cling to both.

Some people run from both.

Some people demand reassurance from both.

And some people spend years learning what it means to build trust with something they love.

The older I get, the more convinced I become that creativity is not just about talent or discipline. 

It’s relational.

The way we approach the canvas often reveals the same fears, wounds, and desires we carry into our human relationships.

And honestly, I don’t think I would have understood that as clearly had life not unfolded the way it did.

Dating as a widower comes with some deeply conflicting emotions. Part of you misses companionship, intimacy, laughter, affection, and connection. Another part wonders if wanting those things again somehow betrays the person you lost.

You ask yourself strange questions:

Is it okay to love again?

Am I trying to replace someone who can’t be replaced?

What does moving forward even mean when grief still lives in the room with you?

For twenty years, I was in a secure relationship. Not perfect. Not free from misunderstanding or ordinary human friction. But secure in the ways that matter most. There was trust. Stability. Consistency. The kind of love where your nervous system can exhale, knowing the other person will stay when things get difficult.

And when you live inside that kind of partnership long enough, it shapes the way you understand the world. You learn to hold a deeper understanding of love, one where opposing forces begin moving together instead of apart.

Passion and consistency.

Freedom and commitment.

Fidelity and desire.

Oddly enough, I think our relationship to art works the same way. It is not built entirely on passion or inspiration alone. It is built on staying. On showing up long enough for trust to form between you and the work.

After losing Nicole, I had decided not to intentionally pursue romantic relationships. Even though I missed companionship, it felt simpler and safer that way. But life has a strange habit of disrupting the stories we tell ourselves about what we are ready for.

And suddenly, I found myself stepping back into the strange world of modern dating with all its complexities: love languages, TikToks, “situationships,” and whatever it's called when someone acts like you're their soulmate right before treating your relationship like a limited-time seasonal offering.

In my day, it all seemed much simpler. You either liked being around someone or you didn’t.

Despite how absurd it sometimes feels, I don’t say that with bitterness. Every generation struggles to figure out intimacy in its own confusing way. We’re all just trying to make sense of closeness, vulnerability, desire, fear, and what it means to love another person without losing ourselves in the process.

Sometimes we enter relationships through passion, chemistry, and emotional intensity, only to discover that the people most capable of awakening us are not always capable of staying.

Other times, something may look perfect on paper, comfortable, familiar, relatable, yet there is no real spark, no aliveness, no mystery pulling two people toward one another.

Sometimes our standards are too high, demanding perfection from imperfect people. Other times they are too low, asking us to shrink ourselves in order to preserve connection.

And somewhere between fear and fantasy, closeness and self-protection, chemistry and commitment, we spend much of our lives trying to learn what it actually means for two people to genuinely care for each other and still move toward intimacy in the same direction.

Somewhere in my attempt to understand my place within the complicated world of contemporary dating, I accidentally stumbled headfirst into the fascinating study of attachment styles.

And what I learned taught me something important, not only about intimacy, but about the relationship we have with our art.

A Brief History of Attachment

Attachment theory is a psychological framework that attempts to explain how our early relational experiences shape the way we connect with others emotionally later in life.

At its core, attachment exists on a spectrum between two opposite relational fears: the fear of abandonment and the fear of engulfment.

At one end of the spectrum is anxious attachment, at the other is avoidant attachment, and somewhere between them is secure attachment: a healthier balance of closeness and independence, vulnerability and self-respect.

Anxious Attachment

Anxious attachment is what happens when someone fears rejection so deeply that they begin abandoning themselves first.

These are often deeply caring, emotionally attuned people who crave closeness and affirmation. But somewhere along the way, they learned that love must be earned, maintained, protected, and managed.

So they over-function.

They chase.

They overthink.

They monitor subtle shifts in tone.

They mold themselves into whatever they think another person needs.

Picture a guy texting his girlfriend:

“Hey babe.”

followed fifteen minutes later by:

“Everything okay?”

followed thirty seconds later by:

“Did I do something wrong?”

Meanwhile she’s just buying avocados at Costco.

At its worst, anxious attachment becomes the slow erosion of the self in exchange for reassurance. People begin accepting ambiguity, inconsistency, or “friendship,” while secretly longing for something deeper, teaching their nervous system that love requires self-abandonment.

If you are willing to become someone’s “maybe” while quietly hoping for more, there’s a good chance anxious attachment is motivating you.

I have a soft spot for anxiously attached people. After experiencing sudden loss, I understand why someone would slide toward this. The fear of someone disappearing is, unfortunately, all too real for me.

But ultimately, healthy love cannot grow where one person must continuously betray themselves just to maintain the illusion of acceptance.

Patterns that reward unmet needs cannot be healed by endurance alone.

Avoidant Attachment

On the other end of the spectrum is avoidant attachment.

Avoidant people are often misunderstood. Many of them are not trying to hurt anyone. Often, they are deeply caring people who learned very early that closeness is unsafe. 

So they develop a different survival strategy: 

Distance.

Ironically, avoidant people often come on very strong in the beginning of a relationship. Romance feels exciting when intimacy is still mixed with fantasy, chemistry, novelty, and serotonin. They can be passionate, affectionate, intensely romantic.

But the closer the relationship gets to real emotional exposure, the more they begin fearing the loss of autonomy, control and exclusivity.

Of course, there are legitimate reasons people leave relationships. Sometimes incompatibility is real. Sometimes trust is broken. Sometimes people simply grow in directions that no longer support mutuality.

But avoidance is different. The issue is not leaving itself. It’s the inability to remain open long enough to move through tension and mental discomfort without running away.

Obligation feels like a trap. Emotional needs feel like pressure. And when they become dysregulated, their instinct is often not to move closer, but to withdraw until the discomfort subsides.

They don’t run because they feel too little. Often, they run because they feel so much.

And what makes this dynamic so painful and confusing is that they often still genuinely care. The feelings are real. Unfortunately, real feelings are not enough if someone lacks the capacity to exist with-in that reality.

Because relationships are not built on emotional declarations alone. They are built on repair. On participation. On the courage to trust something deeper is unfolding.

Avoidant attachment often creates a painful cycle of closeness followed by withdrawal precisely when connection is needed most. One moment there is warmth, vulnerability, and talk of the future. The next: distance, confusion, and random heart emojis punctuating months of ghosting. Not necessarily because love disappeared, but because intimacy itself began to feel overwhelming.

Over time, the relationship stops organizing itself around connection and begins organizing itself around self-protection.

Unfortunately, love cannot grow indefinitely inside ambiguity. At some point, healthy relationships require clear communication, and a shared willingness to move toward clarity together. Otherwise, the very strategies people use to protect themselves from the perceived loss of freedom end up reinforcing the loneliness they were trying to escape in the first place.

Slowly, the trust-fall of authentic love gets replaced by hollow hook-ups, performative detachment, and rigid gender scripts where emotional honesty is treated like a liability instead of the very thing that makes intimacy real.

Secure Attachment

So far, I’ve painted a pretty bleak picture of human relationships, but there is hope. Attachment styles are not fixed. They can be examined, practiced, healed, and slowly reshaped into something more secure over time.

And while secure attachment may be the goal of a healthy relationship, secure people are not perfect.

Secure attachment does not mean emotional invulnerability or the absence of conflict. Secure people can still become hurt or unsettled when relationships become inconsistent or unresolved. The difference is that they tend to move toward honesty, accountability, and repair rather than control, self-abandonment, or withdrawal.

Secure attachment does not mean “moving on” easily. Nor does it mean endlessly soothing another person’s anxiety.

It means responding with consistency without softening boundaries. It means not disappearing from oneself, or from the relationship, the moment things become difficult.

Secure people tend to believe that most conflicts can be worked through compassionately. They can express needs directly without manipulation or games. They apologize when necessary, remain emotionally accountable, and understand that closeness is built through participation, not control.

And perhaps most importantly:

They can love deeply without surrendering their own self-worth.

Securely attached people do not beg someone to stay who continually discards, downgrades, or destabilizes the relationship through inconsistency and mixed signals. Yes, they want to be wanted. They desire reassurance, intimacy, and mutual devotion. But they also understand that another person’s inability to meet them fully is not a measure of their value.

Secure attachment is not the absence of wounds, fear, grief, or uncertainty. It is not manufactured confidence or stoic detachment.

It is the ability to remain emotionally honest in the presence of those things.

It is learning how to stay open without becoming self-destructive. It is learning how to tolerate uncertainty without retreating into emotional obscurity. It is the ability to be vulnerable enough to share doubts, fears, and weaknesses without believing they make someone unworthy of love.

Because secure people understand something essential:

That true love and intimacy is not built by avoiding risk. It is built by two people willing to stay long enough for deep bonds of connection to take root.

For You, the Artist

So what does dating, attachment styles, heartbreak, and emotional vulnerability have to do with art?

Good question.

Honestly, I’m still figuring out what it means to be a single widowed dad who still longs for real connection.. After more than twenty years of being happily married, I’m hardly an expert on the strange complexities of modern dating.

But attempting to understand attachment styles has caused me to reflect more deeply on my relationship with my late wife, the beauty and strength of that union, as well as the places where we struggled to meet each other fully.

Loss has a way of doing that.

When someone dies, you don’t just grieve their absence. You revisit the relationship itself. You replay the moments you were present and the moments you withdrew. The times you loved well and the times fear, stress, exhaustion, or self-protection quietly shaped the way you showed up.

And if I’m honest, I think survivor’s guilt is often tangled up in that reflection.

The painful illusion that if we had only loved better, communicated better, or understood ourselves more clearly, perhaps loss would hurt less or the ending would somehow feel different.

But I also think there is something sacred hidden inside that ache. It reveals the depth of our participation in another human life.

Their absence magnifies the dependance you had on them, it exposes the places where you failed each other, but also the ways in which you stayed. 

You begin to see how intertwined your lives truly became.

What you carried for each other. The wounds you helped heal in one another. The strengths that sustained each other when life became heavy.

Bonds that only become visible in the privation of the relationship itself.

My reentry into dating has made me realize this truth extends far beyond romance or grief. Human beings are relational creatures. We do not simply move through life observing the world from a distance. We are constantly participating in it, shaping and being shaped by everything we love.

And perhaps that is why this reflection changed not only how I understand human relationships, but also how we enter into participation with our creative lives.

In many ways, we date our art the same way we date people.

We pursue it.

Avoid it.

Breadcrumb it.

Use it for validation.

Fear disappointing it.

Fear being seen through it.

And sometimes, if we stay long enough, we slowly learn how to build trust with it.

Some people become avoidant with their art.

They can fall in love with inspiration, possibility, and excitement. They can rush in passionately, buy new supplies, start ten paintings, and feel electrified by potential.

But the moment the work asks something deeper, consistency, vulnerability, discipline, failure, patience… they disappear.

They “friendzone” their art, giving it just enough attention to keep the fantasy alive without any real devotion.

They love the seduction and emotional high of art without the long-term dedication required to truly master their craft.

But unlike human beings, art itself is remarkably secure.

It does not chase you. It does not manipulate distance to make itself more desirable. No amount of withdrawal or manufactured scarcity will lure it into pursuing you harder.

If you abandon your art, the loss is not felt by the canvas nearly as much as it is by you.

The tragedy of neglecting art is not that it stops loving you, but that you slowly lose access to the part of yourself that only emerges in relationship with it.

Because art remains where it has always been: waiting patiently for honesty, participation, vulnerability, and return.

And if you stay long enough, through frustration, doubt, and failure, it will meet you with something most avoidant relationships never can:

Trust.

Other artists are anxiously attached.

They ask art to provide their identity, worth, significance, and proof of existence.

Every painting becomes a referendum on whether they are enough.

They chase recognition the way anxious lovers chase reassurance. They shape-shift constantly, trying to become whatever they think the art world will approve of.

They don’t create from fullness. They create hoping art will finally fill the emptiness they carry inside themselves.

And eventually, the relationship begins to collapse under the weight of that expectation.

Because if you burden your art with the responsibility of defining your self-worth, it will eventually begin to feel less like a relationship and more like a performance.

Art stops being an act of discovery and turns into an anxious attempt to stabilize identity.

But art was never meant to exist solely to maintain the façade of who you think you need to be. It wants collaboration, not performance. Connection, not control. Presence, not perfection.

And the tragedy is that no amount of success can heal a relationship built on unhealthy attachment.

Not with people.

Not with creativity.

Not with art.

Because healthy relationships, whether romantic or artistic, cannot survive on fear, emotional distance, self-abandonment, or the constant need for approval.

They must be built on something much deeper than safety alone. They must be built on two people freely choosing one another, again and again.

Because art itself is intimate.

Every blank canvas asks the same terrifying question love does:

Will you stay present long enough to let something real emerge?

Will you remain when the excitement fades?

Will you continue when uncertainty enters the room?

Will you remain open long enough to discover who you are becoming without losing yourself along the way? 

That’s the real work.

Not simply learning how to paint.

But learning how to remain connected to something meaningful without controlling it, fleeing from it, or demanding that it constantly validate your existence.

Art teaches us how to walk the difficult line between passion and discipline, between freedom and responsibility, between self-expression and surrender.

And maybe that’s why art matters so much.

Because when we stop using creativity to escape ourselves, prove ourselves, or protect ourselves, something extraordinary begins to happen.

The relationship deepens.

The work begins to expand beyond us.

And maybe, slowly, brushstroke by brushstroke, the secure bond we build with our art will transform the way we live, teaching us that the deepest forms of love are not built on fear, performance, or escape, but on presence, devotion, and the willingness to stay.

The affairs of the heart are complicated, messy, and often painful. Yet hidden inside that vulnerability is the very thing that makes us feel most alive.

And perhaps that is what art has been teaching us all along:

that our relationship with it is not merely about making things, but the practice of love itself.

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If you’re an artist searching for deeper connection, honest feedback, and a more meaningful relationship with your work, I’d love to walk alongside you. Explore mentoring through The Painted Path Studio.

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