Writing

The Tao of Loneliness

Misadventures In Being Authentic in Dating

Photo by Noah Silliman on Unsplash

“Loneliness is the human condition. No one is ever going to fill that space. The best you can do is know yourself; know what you want.” — Janet Fitch

She fumbled for my hands as she danced with me. I could see she was drunk and completely out of sorts. I’d often had inebriated women press up against me on the dance floor in an unwelcome and uninvited ways, but there was something manic and pained about her movements. She was there to forget something and not dancing to feel joy. She was there to feel something different than what she was drowning in. She stopped, looked up at me with tears welling in her eyes and cried, “I miss my ex-boyfriend so much!” I felt her pain, and could do nothing but pull her close and hold her in some vain attempt to offer comfort. I wanted to communicate that I understood her loss. I knew all too well what being alone meant.


My whole life I’ve sought for a partner to share it with. I haven’t been looking for someone to complete me, as the oft unhealthy and sappy love stories pine for. I’ve simply wanted someone to be a companion for the journey. But through it all I’ve never really felt very loved or wanted. Sure I’ve had short periods that felt like I was loved, but most of my life has been me alone against the world. Much of my life I was mired in being very obese, but in the last year and a half I dated a lot, having the benefit of trying out finding love as a fit man. I had a number of fairly short relationships, but none really reached any true depth that I have wished for.

Dating again started out to be an intrepid adventure, with the excitement of first kisses, and first other thing. I met so many amazing women who found me physically attractive for what felt like the first time in my life. I met some with glaring red flags, and was clearly the comparable red flag for others. Through it all I did make mistakes and ended up hurting some women, completely unintentionally. In all the dates I had, I never once did or said anything I didn’t genuinely feel in that moment. I was, and presented myself as, the person I really am. I strove to be authentic, honest and vulnerable, because I wanted to be loved for who I really was. I’m a bad liar, so why bother? I could pretend I’m some exotic, dashing, mysterious man of intrigue, but most nights I just want to hold someone close and be loved.

I do understand much of why things didn’t work out for me. For many, I simply wasn’t what they wanted. Some wanted someone who would spend a lot more money on them, whether if be expensive getaways or simply to be their sugar daddy. Others wanted someone more attractive, as my body will still be a bit dad bod even when properly pumped. Still others wanted things that I simply couldn’t give or provide for them. For so much of my dating I simply was drained of time, money and energy, and I felt all the more alone as a result. With some exceptions, I don’t fault any of these women as I am complicated in my own right. My demisexual nature means it takes me a while to warm up sexually, and that can be seen as disinterest to those who are unfamiliar or impatient. I have also been hurt very badly, and while very much emotionally available I can be spooked by clingy and irrational behavior. Trust is not immediate and feeling safe with a woman is something I no longer take for granted. I’ve had women that wanted me to be sensitive, but when showing that I was in fact very human and possessing of a life with a share of traumatic events, they would dump me with patronizing comments like, “Sorry, you seem like a great guy. You should get therapy. Bye,” before blocking me. My therapist got a chuckle out of those conversations.

Throughout all of it, I did see the hazards of being a naturally giving person. I truly enjoy pleasing my partners, whether in remembering little things and surprising them with special evenings, sincere affection and even just pampering them. I’ve given so many massages, but only received one in the last decade, from a friend who is a professional masseuse. I’ve made so many evenings about a woman’s happiness, enjoyment, and yes, pleasure. I often struggle to ask for what I want, initially because I didn’t know what I wanted for so long. Later, asking became difficult because it was either rebuffed, or acquiesced to in the most dispassionate and often annoyed ways. As a man, I’ve had to ask a woman to stop doing something sexual to me, because she was doing it intentionally painful. Attempts to communicate the problem resulted in indignation over her technique, though most likely this was in order to get out of doing anything but receiving ever again. That makes me nervous for the next woman’s possible actions. Even in the context of kinky relationships, women wishing to be submissive often felt more about wanting to be selfish and pleased, rather that reciprocal play. For many people the moment they find someone generous, they decide they’re going to get there’s and not give back, since so many have hurt them before. Great, I get to be the one used and pay for the sins of their other past lovers. That is something I could never do to another. I’m all for treating a woman like a queen, but if I’m relegated to court jester all the time and am never also treated like a king, it’s time for abdication.

No one is without complications and everyone has a past. Very few people past 30 don’t have some baggage, but some people have seven piece matching sets. The trick is to find someone whose crazy meshes in a compatible way with your own. The last woman I dated proved she was selfish despite believing herself generous, and I simply gave up on dating. I’ve never felt lonelier than when with someone who didn’t really care about me. I’ve felt that my whole life. My own family didn’t want me and let me know it often. This takes a toll on your spirit, and you find yourself wondering why bother.

I stopped looking for The One™ a long time ago. I quit seeking for a partner, too. I even gave up hoping for a lover. I’ve reached a point where I just want a close friend to do things with, take a dance class, go try a interesting restaurant, see a concert together or visit an art gallery with. There are apps to find sexual partners, and romantic partners, but it can be hard for an introvert to connect with a woman just for friendship. Lack on human companionship can be very difficult to tolerate. I’ve never really bonded with with guys other than in a work environment, and most women rightfully questions a man’s intention toward them. Funny thing is that with me, I don’t give it up that easily. Now I don’t give it up at all.

So am I to be a lonely monk that walks the West seeking to help others in their plight? Why not, to a certain degree? I go dancing, by myself, every chance I get and dance with others. I take photos nearly daily to share with the world, to see beauty in mundane things. I paint artwork, poorly, and pen the occasional article here to try and help others. I try to explore the world one day at a time, and try to makes the lives of others better around me. I try to smile, even when I don’t feel it, hoping maybe it lifts someone’s day. I listen to people, and if they need a friend I’m there for them. I do what I want to do with my life, and refuse to stop living. Yes, I feel down and lonely often, but I still try to connect, even if only on the most superficial ways. I sometimes feel more like a catalyst for people, maybe some remote archetype, that helps them learn more about who they are. I guess I am that wandering monk … I even have the shaved head!

At the end of it all, I remain authentic and I am who I am. I’m not waiting for someone to live my life with, I’m just living it. I do my best to be a good person, a good father and to be a good friend to the many people that come through, and leave, my life. Who do I turn to when I’m hurting? I journal and I poor my feelings out in creative works. I dance the loneliness away, and often. I try my hardest to be someone that makes people smile when they think of me.

Loneliness is a part of the human condition. We really are all islands unto ourselves. But rather than be a desert island, I do my best to populate it with something beautiful.