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{ A note to the reader: The music I primarily listened to while writing this essay is The Meaning by Desert Of Hiatus. I invite you to listen to the album while reading it.  Also, for readability and collection purposes, I have made this essay available as an ebook – ePub, MOBI, or PDF. Click here to access those formats.}

Loneliness Returns

Loneliness has returned. Its often-gentle, but mostly constant ache—present and full in my body, yet empty like a little hole in my heart—is growing in my soul. It’s dense and magnetic, colouring the little-nuanced qualities of my many daily moments alone. Every so often, it collects into a full emotional immersion and becomes my whole world.

Of course, being lonely isn’t new—I know it well—and it isn’t as though loneliness and I have been estranged long enough for my mind to forget the intricate solemnities of its presence. It’s just that recently it has emerged with a nostalgia for that magical call to love, a call that once embodied my will and way in the world. This call is born of an aspect of myself that I put away two years ago; an aspect I had all but considered dead and thankfully buried beneath time and hard lessons. Yet, here it is again. Loneliness is asking me to remember that deep eros, as if to put back on an arm I had almost forgotten I couldn’t get by without.

But there is a reason I put it away so long ago.
The story goes like this…

The Tragedy Of Loving

In the past, feeling a loneliness like this would unconsciously drive me. I would move with a sense of emptiness I sought to fill. I would let such feelings manifest a subconscious belief that what I lack is love, and my fill is to be found in someone else, somewhere outside of myself.

Within this belief was a preconception of who and how that someone else will be, my “perfect woman”: an illusion co-created by the unique character of my soul, my societal conditioning, and the examples of what love means and how love is lived provided by my early familial relationships. I would carry an image of this construction around, holding it up to each person, checking to see if it fits. Eventually, finding someone upon whom it fit just enough—someone whom I likely fit just enough for them too—and they became the avatar for my perfect someone. They became the light to love me through my lonely darkness and together we would fall in the blisteringly, blissful, bastion of romance.

I let the enthusiastic cascade of infatuation blind me from who this person might actually be while I subconsciously endeavoured to conceal all the otherwise apparent places where they did not fit the unrealistic image of my perfect woman. I needed to aspire against reality because I needed to keep believing in this mythic thing called love, this thing that could only come from my perfect match. I would compromise and sacrifice and strive to disregard the inconsistencies between who they were and who I wanted them to be so we could hold on to that love. It worked, we would fall into each other, craft a cult of two, and warp reality around our desires.

That high of early love was incredible, but it never lasted. Once it wore off, the image faded and the cracks in my illusion opened to the truth. All that seemed to be left was pain and we—out of deep longing for love and a profoundly poor education on how to do it—usually hurt each other, as an extension of this pain, all the way to uncoupling.

[Side-note: In fairness, this story certainly lacks the explanatory depths needed to give true merit to the richness that each fall offered, as well as the complexities of the non-monogamous lifestyle that accented the last decade of my life. Also, the underplot of this story has not been the rule for all my romantic entanglements; not all relationships have transpired according to this underlying narrative. Some have managed to stay golden in the light of ephemerality and distance, and others still, found a shift to new heights of connection despite the death of our romantic embrace.]

Only Broken

The last time this story unfolded, the final climax of uncoupling was nestled in months of poor communication and mutual mistreatment, each of us desperate for something the other could not offer. The vortex of frustration, pain, and confusion consuming me in this process was so overwhelming that something broke inside of me. Something about who I thought I was—and what I believed to be love—went away. In its place was a belief that the very feelings that I once associated to being in love were merely echoes of profound wounding from my ancient past, stuck inside of me as though these wounds were always present and pending.

When that something broke, I felt, all of a sudden, that I had never truly known love. I had only ever known desperate attempts not to feel lost and lonely, coupled in a cult of two. The trust I held in what I thought was love immediately vanished. Every inclination of feeling that I might, in the past, have thought of as love became suspect. Those feelings became the strategy of a child protecting itself from a lack of love while habitually attempting to recreate the very context of relationship that led to the aforementioned story in the first place — because that’s where the love was and now it’s the only love I know. But it wasn’t love. It was never love. I was never love. I was only broken.

As painful and upsetting as that realisation was, and the context that gave birth to it, somehow it was indescribably freeing as well. All of a sudden, when that something broke, it broke into something new.


Something New

I put the call to love—the call to romance, the call to dissolve myself into that hormonal deluge pumping into my bloodstream from the site of the wound left by cupid’s poisoned arrow—away, and instead, I travelled with that something new. I travelled curious and exploratory, for nearly two years.

During this time I came to embrace my capacity to be with women in intimacy and pleasure and presence and honesty and clarity and trust and healthy dynamics, but always with caution. Always with one foot on the brake. Always suspect of anything that felt like that thing I once thought was love—which was now just dysfunctional hurt waiting to happen.

This suspicion was a gift. It redefined the context by which I entered relationships and enabled me to explore connections I might not have otherwise. It gave me the inclination to explore what different feelings might mean, what different calls to connect may manifest when explored in transparency and authenticity. It offered intimate connections that felt easy to embrace. I wasn’t set up to feel insecure or unsafe, like my wounds could be seen or salted, because my guards were always high.

This process of suspicion has all gone very well, and I feel I have, in the process, cultivated a sense of inner-security and confidence I hadn’t previously known. In fact, I had the most emotionally successful polyamorous relationships of my life these past two years—communication, compersion, community, and the collective celebration of intimacy amongst friends. Truly, a gift.

In all of those intimate explorations, one thing has remained a constant: my sense of self. Each of us came together as whole and complete entities; self-responsible adults; individuals sharing pleasure, joy, and connection. “Finally”, I thought, “moments of intimate connection and trust are coming into my life that aren’t ultimately usurped by the profound tendency towards codependence sewn into my sense of self and the social world around me. This must be what it feels like to be stable, secure, and interdependent.”

However, I began to see that although the foreign policy of my self-contained and well-protected island of a person has, on its own merit, deeply fulfilled me, and still does to the same degree, a new area of potential fulfilment has opened up.

Something new has come again, and it’s calling for love, but differently than before.


Love Is

Love—as it is described by one of my favourite philosophers of love, David Deida—is “what is when your heart is open”. To love is to have an open heart but to be in love is something different. It is what he calls romantic attraction and “because romantic attraction is based on qualities of your partner that you unconsciously recognize from your childhood experiences, you will be as fulfilled and as unfulfilled by your partner’s love as you were by your parents’.”[1]

Our relationships in childhood are the unconscious model that we carry with us for the world we grow into. Unacknowledged, we repeat and reinforce those relationships models indefinitely. If we were broken in childhood — as most of us are, despite our hopeful attempts to pretend differently, embedded in a culture that lies to itself to tell us we’re okay — we will carry that wounded past with us in romance. If we do not discover our wounding, those wounds will be the only love we know. We will only be broken when in love.

Over the last two years I have experienced many beautiful moments of connection, but none where I truly opened my heart. I was always guarded, even if ever so slightly, for fear of what felt like the mistake of falling in love and for fear of the mistakes I’ve made in love—how I have behaved and treated others; how I have allowed myself to be treated; and the unstable emotional grounds upon which I once tried, foolishly, to co-creatively build a cathedral wherein love could be celebrated.

I was so tired of all the hurt that falling in love created in my heart—and in the hearts of those I was opening with—that I shut down my heart for a time. I put love away. I needed to get clear on who I was and grow into my adulthood more fully (in secret, subconscious hope that if I did, I would be able to attract my reciprocal, and finally find that true love that I believed I had never really known.) In doing so, I discovered different aspects of myself and my potential for connection, as well as lateral areas of my heart that, when I had only focused on depth, I had missed.

Yet, in shutting down the depth of my heart, I misconstrued something important that my recent loneliness has allowed me to clarify. The love I felt with the women of my past was not an elaborate, but foolish lie I told myself to protect from despair. That was love, albeit immature, but still love, true and real love, and I am goddamn lucky for it. The hurt that came with that love, however, was equally real. And dear sweet God, it’s easier to dismiss the love and pretend it wasn’t real at all than accept the devastation that came with all that heartbreak.

Yes, due to our mutual immaturity—sometimes more me, other times more them, often a dancing balance of 60/40 back and forth between us—we often parted ways, wounded. As in love fell away and the dysfunctional relationship patterns indoctrinated by a traumatic society expressed themselves in our dynamic, our open hearts couldn’t handle the hurt we carried from our past. Nor could our minds keep clear about what pain came from whom, where or when, or what it meant to heal and hold support for healing in one another. However, the reality of our wounds does not contradict the truth that that love, that opening into each other, is always meaningful, real, and transformative.

Two years ago I was hewed by the painful dying of a romance and all the shitty behaviours that emerged in the process. In the time between then and now — while I explored the vast potentials for connection made possible when the subconscious prioritization of old love patterns were called into suspicion and used as the reference point of where not to go — something truly meaningful and important came to light, and that light has grown so bright that it is now shining upon that which I hid away to heal: that something that broke inside of me, was my heart.

With each broken heart comes the pain from each break that came before. This most recent one was not only a cumulation of all the pain from heartbreaks past, but also carried with it wounds so deep I saw the very essence of heartbreak, the very first place my heart broke. It took me to a place so far back I only have scenarios to describe its later contexts, personality tendencies to illuminate it, and psychological concepts to explain it. There was too much anguish at that moment to be with and acknowledge that heartbreak — it was too much, too fast, too soon — so I pretended my love wasn’t real because it was easier than facing the immense gravity of those wounds. Recently, thankfully, I have been able to acknowledge this, come to terms with it, and learn a lot in the process.

Of course, this is not just about me. I understand that the pain of heartbreak does not exist in a vacuum. Each one sewn into the tapestry of my adulthood was shared with another, and I am remorseful for the role my mistakes played in each heartbreak I helped create. I am, in turn, doing my best to be increasingly more responsible for my actions in the present, and of the past. However, I am not ashamed to have made these mistakes. What good would shame serve me in this context? I might be responsible for myself, but what happened between us was not my fault, nor theirs. We were co-conspirators in the downfall of our romances, yes, but we were also perfect pawns for generations of relational dysfunction, en mass across society, battling on the front line of change in the light of the postmodern world. Furthermore, my strategic adaptations to each heartbreak led me deeper onto a path of learning what it means to love, each mistake a was ripe opportunity to heal and grow. Why should I be ashamed of mistakes that I have learned from and better myself by?

Reflecting on my loves of the past as real and true — if only in context — has invited me to reflect on what each one has meant. I can see that some of those loves were sick or unsustainable and I am glad to have grown away from them. Some of those loves were perfect as they were and as they ended, whole and complete stories onto themselves. Others grew different over time and became great friendships that I am glad to know I can cherish for the rest of my life. Others, however, have a bit less resolve; the ones that weren’t quite love but may have been if I hadn’t been so afraid of hurting and being hurt; the ones that leave me periodically wondering if I walked away a fool for not having given up the game of self-protection and surrendered into the gorgeous tempest of romance.

Which brings me back to the loneliness at the outset of this personal essay.


Wrestling Loneliness

“The crucible for meaning in your life is in how you wrestle with the way things are”
– Stephen Jenkinson[2]

I have come to discover that this loneliness is not a singular entity come to clandestinely manipulate my world, but an amalgam of emotional nuances intricately crafted together. It is an alchemical mix of alone, sorrow, sadness, and grief — the feelings at the root of romantic bliss and hurting and heartbreak. It is an acme of particulars, greater than the sum of its parts, manifest as a present-tense longing for a romantic embrace into which I can open my heart again.

I don’t know exactly what this recent loneliness and the revelations it brings will mean for me or my heart, or what it will teach me over time. I have only an inclination as to the emotional space I am navigating as I progress through the layers of my wounding and into a slowly growing relational maturity. Like the initial decision to put love away, a suspect, and like any significant shift in one’s inner life, I cannot see the true meaning of it all until that meaning is forged by my relationship to the process —anodized by the choices I make in how I respond to the way things are, an extension of all that I have learned in time and practice. All of this is new — ancient human tendencies amidst fresh psychoemotional context.

Unlike my past, however, as the complex loneliness of late — the way things are — amasses within me, I can recognise that it is not a problem to be solved by the love of someone else. I am not struggling against it in desperate attempts to make it go away, but instead, I am embracing it. Having done so, having welcomed it in as if to say “hello, sweet loneliness; how are you, and what lessons have you brought for me?”, I realised something that feels important (which became the inspiration to write): my loneliness is not a lack of love, a need only fulfilled by the love of another; it is love.

Love is not an instinct, nor perhaps is it even a feeling. It is not something that happens to you; it is something you do. Love is an art, not an acquisition. It is a skill, a practised capacity of opening one’s heart to allow the world outside to come in and touch us in the places we are most vulnerable. The places where it still hurts despite the adage that time heals all wounds; the places from which our greatest capacity to feel reside and the places from which we manifest our greatest capacity for an ardent life.

To practice my love when alone is to be with this loneliness and to know, in the depths of who I am, that this loneliness is not so much a longing for a love I don’t have as it is a refraction of my capacity to love and to share love. By the choice to celebrate and allow the longing and loneliness to fill my being and consume my awareness, and not to resist or distract or pathologise or seek to answer it like a problem needing an external solution, I train my nervous system to know safety where it once only knew danger. I grow my capacity for love and to craft love into my world.

The art of love can be, and often is, the art of longing, the art of loneliness, a practice of allowance and surrender and accepting the lessons of heartbreak.

To long is to open the heart to honest hurting; it is to open the heart to one’s self, and to open the heart is to love; and thus to long for love is to know one’s own love and to practice the art of it. My loneliness is not born of a lack of love. It is not an emptiness but a fullness. It is the canvas upon which I practice creating the masterpiece that is my love, that perhaps one day I will craft with the heart of another as well, and together we can decorate the walls of a cathedral (relationship) we build together to hold the creative elegance that is our love-ing.



Yes, I desire romance, a lover, a partnership, to give falling in love another try with faith that all that I have learned might allow me to do so with my maturity intact. But although this expressed desire is the meaning that my feelings, and the mindset I am embracing them with, are giving birth to; the broader psychological context in which such a desire exists is complicated, to say the least.

First off, my internalized polyamorous social climate invites some shame in me for admitting this desire — perhaps because somewhere in our collective process of deconstructing default monogamy we decided it was weak to not be an individual and completely self-contained with no desire or need for partnership; and any need is a pathological desperateness for connection that will only consume you both. (In fairness, my past experiences have illuminated this as potentially quite right, and I sometimes wonder how many people are poly as a strategic defence against facing the pain surrounding such desperation, while building new relational structures rather than correcting the broken ones they were given…) But I desire partnership nonetheless, and what a blessing it is to be willing to approach the throws again, not despite, but in honour of all the heartbreak that has come of it.

I certainly do not desire irresponsible yielding of boundaries, childish behaviour, fantastical dissociation from reality in an effort to sustain a mutual lie, and all the rest of the bullshit that my old story once ushered into my life. I seek in no way to repeat my past any further, or rush into a partnership for the sake of longing, loneliness, or poetic ideals. Nor do I want to allow the mistakes of my past to continue to forge an inner-context that disheartens the potential for something greater than brokenness, pain, and desperation in the dance and dynamic of romance and partnership.

I also have fears: the fear that I am not as mature as I think I am; that any attempt at romantic loving will only end in similar cadence as each one that came before it; and that I am destined for heartbreak no matter how skilful the entry. But it was the tendency to be moved by fear, the fear of hurt at the core of my ancient wounds, which brought the old story into existence. So if I am to embrace romance and partnership again, I need to do my best to be courageous in facing these fears, in meeting my wounds. I need to trust that having uncovered and come to know the wounds of my past may free me from their unconscious control, at least to some degree, and I could be, we could be, more than broken in love.

I know there are still wounds in me, waiting to be felt in the context of secure connection, with an empathic and supportive witness whom I trust and trusts me in return. There are wounds to heal but perhaps, just maybe, I have matured enough to trust and feel safe and build a context in which that healing can take place; matured enough not to recreate the past by way of an unconscious prioritization of connections with people who will help play the old story out in the same familiar way.

Perhaps, in practising this art of longing while I continue to cultivate maturity in the other areas of my life, I will one day meet my reciprocal. Perhaps, if such a relationship could be found and forged, we will be able to trust each other enough to open our hearts together, support mutual healing, and weather the storm that will be the inevitable dying of romance, while staying in loving partnership nonetheless. Perhaps, we could craft something on the other side, surrendering into something beyond each other. Something that, like loneliness, is greater than the sum of its parts. Perhaps, I am a foolish idealist.



Again, I don’t know what I will learn from all this, or if anything I have written here will still hold true in the light of the something new waiting for me at the end of each stage of my life. There are so many complexities to love — mine, yours, and the higher force of love itself. I make no claims that I know what’s true in all of this. Nor does what I have written here outline a full picture of all that I have felt, am feeling/learning, or have passed through in love and heartbreak. This response to loneliness may be a revelation of maturity or a defensive adaptation to pain. I don’t know yet. But whatever it is, it feels like good learning.

Thank You For Reading This Essay

I must admit that this is, by and far, the most vulnerable price of writing I have released up to this point in my career. It took a lot of soul-searching and conversation with my editor, Olenka Toroshenko, to help me muster up enough courage to do so. If it wasn’t for her encouragement, and her help in the editing process, you would not have read it. Thanks, Olenka.

I also want to thank my patrons on Patreon. They are a collection of people who believe in my work (my writing, public speaking, and podcast) enough to pledge money to me each month, empowering me to keep investing in this work. It is with their trust and their support that I have had the time necessary (about 60 hours) to produce this essay for the public eye, as well to pay Olenka for her essential editing.  Thank you, patrons.

Finally, if you enjoyed this writing and have received value from reading it, please consider supporting my independent writing career by becoming my patron on Patreon, or by leaving me a PayPal donation. Everything I do is predicated on my content being free to enjoy, but community-funded. Without the financial support of people like you, I could do what I do. Thank you.

With love,
– James W. Jesso

[1] Quote from ‘Intimate Communion’ by David Deida — published 1995 by Health Communications, Inc. Deerfield, Florida

[2] Quote from ‘Die Wise: A Manifest for Sanity and Soul’ by Stephen Jenkinson — Published 2015 by North Atlantic Books, Berkley, California


  1. I appreciate you posting this and sharing your process. In many ways it mirrors my own experiences and process as well.

    Recently I had a Bodynamic Bodymap done, and it showed that I have developmental trauma from my Love/Sexuality childhood developmental phase (age 3-6) at the muscles that physically/and emotionally support the heart from the back (serratus posterior superior). In the Bodymap it shows I have deep resignation in these muscles which essentially means I have a hole in my heart, which leads to the feeling of being heartbroken. Due to the collapsed state of this physical/emotional part of myself it creates deep feelings of loneliness and longing for the hole to be filled by another.

    I have not resolved this, but I am starting to form clues from the therapeutic work I am doing that the solution has to do with building/developing a contained and supported (by other first, and then self) heart. One that can’t be given away, but one that exists in a state of compassionate mutuality with another.

    It sort of feels like I am constructing a new part of myself, a new heart one I can actually own, that has never existed before. Trying to sense the boundaries of my heart energetically front and back as it is physically located within me, has been helpful in this process. In therapy having the therapist put his/her hands on the front and back of my heart to help me build and sense the container of my heart has been good, although it puts me in touch with the agony of the emptiness inside. Affirming this agony; giving it room by myself and the therapist; also being an important part in this healing process.

    Building a heart that “I never had” is challenging, it sort of feels like learning a new language or skill. My sense is once the container is built more fully, it will start to fill itself from the inside out. It will become a source of “love” energy rather than feeling like the absence of it. I say this because of other developmental traumas I have healed from even earlier stages, had followed a similar path in terms of the felt sense of building a new emotional resource.

    It is so easy to fall into the old pattern of heart-aching longing. Coming back to myself and sensing the bounds of my heart helps, the agony is still there, but at least it’s not pouring out like an unstoppable vortexial consuming river. Having compassion for the contained pain in my own heart helps tremendously as well.

    I can’t understate the importance of when working with difficult feelings and emotions, especially heart based ones, to sense the energetic boundaries of these. Otherwise it can often feel like it engulfs your entire reality, and as soon as that happens many defenses arise to come to the aid of the ego in order to try and maintain some kind of integrity. For example longing itself is a kind of defense against the sadness of the feeling of loneliness of the heart being unseen, unmet & unsupported.

  2. It’s going to take a few rereadings and some deep ruminations to fully appreciate the fine-tuned message contained within this essay. It struck so many chords with me as I read through it I felt as though I was reading the musical notes of the song of loneliness. As a fellow man I thank you from the bottom of my heart for your courage in opening up with a degree of grace and probity rarely found in any media these days, especially media authored by men. This is why I support you. You’re doing the hard journeying into the human condition and bringing forth discoveries gilded in an eloquence that can only come from thoughtful consideration of interpersonal rel ationships, deep self-reflection, and a continually cultivated relationship with the unconscious. These will help others along on their own journey.

    I know, at least for myself, that it’s difficult and energy intensive to write about these weighty topics but I’m always looking forward to more from you. Hope this ends up being a continued subject of your writings.

    Keep it up man.

  3. The article mentioned above quotes Prime Minister May of UK: “For far too many people loneliness is the sad reality of modern life…. I want to confront this challenge for our society and for all of us to take action to address loneliness endured by the elderly, by carers, by those who have lost loved ones —- people who have no one to talk to or share their thoughts and experiences with. ”Loneliness is most common among the very elderly and the adolescent.

  4. davidorban Reply

    In The Postmaster by Rabindranath Tagore we have the theme of loneliness, happiness, gratitude, connection, memories and guilt. Taken from his Collected Stories collection the story is narrated in the first person by an unnamed narrator and after reading the story the reader realises that Tagore may be exploring the theme of loneliness.

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