May 12, 2021

Why do Men Cheat? Why does Anyone Cheat? Many Reasons.

This is the third article in a four-part series. Read part one here, and part two here.


My first sexual experience was with a prostitute.

I had sex before I masturbated.

Sexuality was somewhat taboo in my home. My parents slept in separate rooms from a young age. Intimacy was not defined in a healthy and clear manner for me, but rather in an unhealthy and detached manner.

I observed my parents’ level of connection and intimacy (or lack thereof) and thought this aggressive separateness was the norm, that men held power and that women should yield to this. It was a long road back to realizing the toxicity and inequitable nature of this belief. Patience was something that took me many years to cultivate, but more on that later. 

My friend at the time, having found out that I’d never had sex, took me to a brothel. I remember being so nervous. My whole body was shaking, tremoring, and I remember being so scared, scared of being judged—I had no real sexual experience. I had no idea what to do.

I feel most men can relate to this for their first time. There is such a stigma attached to men in general that they “should” know life. That we need to know how to be and do in the world and if we do not we are “less than.” Irrespective of whether one has never had exposure, if a man doesn’t know how to have sex or be with a woman, that’s considered unmanly.

The tension men feel from this ludicrous pressure is so damaging.

Ejaculating consciously for the first time was so weird for me, almost painful. Such a strange experience. I felt a myriad of emotions that I was unable to process at that time. My friend asked me how it was. I lied to him, told him it was great, but it was not. It felt disconnected and simply foreign to me. I experienced a lot of inner conflict from that moment—moral, physical, emotional, sexual. I truly felt lost. 

But that was not always to be the case…

Women, sex, the sex industry, prostitution—this became familiar escapism moving forward.

I became further disconnected from healthy masculinity and began to objectify women, myself, people, and life as a whole. My body and nervous system quickly figured out that I could experience pleasure in my body without worrying about being rejected, or not being enough, or being humiliated. I was all in on that. 

When I was stressed, tense, felt lost, was angry, or needed a distraction because I felt shame around my failures in relationship, business, or in life, I would seek sexual pleasure.

I would go out, engage in one-night stands, and if I found nothing there, I would visit an escort or an oversexualized massage parlor. I used my credit card, spent money recklessly, justified my behavior in every way possible, felt the guilt and shame, and cycled back into the same actions over and over again.

I became more distant from my family and began to love life at the expense of suppressing, ignoring, and pretending my pain, fears, and family issues did not exist. I grew comfortable, charming, held a zest for life, connected much with women, but something was missing. I was missing some…substance. I moved deeper into physicality and mind and further away from the depth of what required attention. 

Entering my early adulthood was an interesting time. I began to redefine what being a man meant, what being masculine meant for me.

How did I wish to show up in the world?

This was a question that intrigued me. I finished high school and I wanted to be in the world—to explore, to experience, and to feel, and importantly, to leave the familiarity of a place that had tainted my view of the world, yet simultaneously provided me with deep connection. I dreamt of one day being away from where I lived, so I created the circumstances to do so. Physical and geographical distance from what was familiar represented distance from my problems, pains, and fears. 

But before I could do this, I needed to become more of what I thought it meant to be a man.

So, I kept drinking alcohol, kept fighting, being hyper-aggressive, violent in my attitude, building the body, and continued my promiscuous behavior in unhealthy ways. After a while, I valued my health too much to keep drinking, so when I was 18 or 19, I simply stopped drinking. I forged my personal identity card with a governmental department so that I could enter clubs and bars earlier than the age of 18. Always looking to be popular, liked, loved, and adored—my behavior appeased others and revolved around seeking subtle or even gross attention. Always giving, giving, giving, and doing things that often did not align with my truth. 

I set off to travel the world and worked on cruise ships. I missed my friends and my grandparents the most. But I had this pull to explore and be of the world, to experience fully and importantly to come back a new man and tell tales of great adventure, women, courage, and power—characteristics that I thought defined manliness and maleness.

I wanted to find love, be loved, give love, find peace, create peace, be a strong, clear, and confident man.

I was always deeply inquisitive and felt that if I went to different lands, I would reconnect to that deeper philosophical self. Yet I still felt self-conscious and disconnected, unable to recognize the value I brought to the world and to myself. This is something so many men are unable to do: be self-compassionate and recognize their worth in a humble manner. 

I felt that if I moved into the world, I would return wiser, be at greater peace, feel a deeper connection to self…or perhaps I would create my “success” in the world and I would never return. My experiences abroad were profound for me. They were life-transformative. I explored, made new friends, and learned new skills. I was with various women who taught me much about myself, helped me to reshape my inner aggression, and transmute it into a greater sense of peace. But I was not quite there. My life was transient. Whilst I was making immense changes, they were all grounded in non-committal energy and intention. I would discover shortly what this all meant. 

I was still visiting prostitutes in secret. I felt shame. I felt wrong. I knew it was all for convenience, validation, ego, and the avoidance of pain and fear. Yet I continued to be this person in the shadows, living two lives. One of “spirituality”—learning from an Ayurvedic master, hiding from him my secrets. And the other in the sex industry, being “a player,” and losing myself in the process. 

I needed to be back home; my family was calling me. My mother and father were both requesting my return to assist in dealing with my brother. His drug habits were worsening to a peak and I could not ignore it anymore. This would be another three- to five-year journey that would yet unravel. 

It was time to face life once again, to come into direct contact with some of those demons of the past. I was tired of being a parent when I wasn’t one, but I chose to appease and impress and get the attention of my father once again. 

That little boy came out—father wounding is something many boys and men deal with (or rather, don’t deal with).

As I returned, I felt free. I felt grounded, peaceful, connected, enlightened, and wiser. Having spent time with amazingly wise individuals and a special mentor, I felt ready. 

Every man needs a healthy or number of healthy men to lead us through our own personal journey of life. When we miss this, we miss the intricate parts of masculinity and expressing our truth in the world in a constructive, empowering, and contributing way.

As a woman, ask yourself if your partner has healthy men in his life who have guided him through difficult times. This will give you an idea as to how he may cope with challenges and how he will relate to you.

If the answer is no, instead of giving to the world positively, we will tend to take selfishly and with an immature (often unconscious) intention to receive what we didn’t get. We have no balance. For most of my adulthood, this was me. Despite appearances and even some healthy aspects, my behaviors were more and more entrenched in the shadows than I could have ever imagined. 

Life was different when I returned home. I was more humble, connected, peaceful, worldly. I was wiser, more open-hearted, and open-minded. But this soon changed. A few months in familiar and once again volatile surroundings and that old pattern of disconnection, hyper-aggression, frustration, and anger become the dominant traits of expression for me. I had lost the essence of myself once again and chose to succumb to this.

And so began a series of intimate relationships and movement through the world that was unclear, without purpose, and dishonest. I dreamt of traveling again and that is what I did. I distanced myself from commitment and taking the time to address my core fears and put a façade of completion and clarity on. I wore varied masks—masks that hid my need to control others, my environment, and life. Masks that hid my oppressive, judgemental, critical, and objectifying behaviors.

I did what I could to initially impress and then slipped into old patterns.

With my friends, myself, and with the women in my life. I was not living in clarity or purpose but appeared to be. I had massive dreams, but these were unfulfilled. I was in dissonance and a state of subtle self-loathing, having never addressed the core of my wounding. I was so “smart,” persuasive, and charming that I talked myself out of doing the work. But this was about to change, fast and f*cking hard! 

Whilst I loved women and was comfortable with them, I did not want to commit. Commitment was scary. When I sensed my freedom was restricted, I felt like I was being annihilated. Detached sexual intimacy was easier.

Still, I yearned for connection. So, I sought it through sexual novelty and thought that this was the pinnacle of connection because of the intense hormonal rush—how wrong I was.

I cheated in every relationship I was in. I had affairs, was sexually promiscuous…I was out of control. I was running from my past, my trauma, and my pain. I needed sex, validation, and the rush of novelty (or so I thought) to feed my ego. It was only much later that I discovered how transcending, freeing, and evolving authentic and cleared sexual union can be.

Why do men cheat? Why does anyone cheat? Many reasons:

Past trauma, unresolved issues, revenge, sex, and/or love compulsion, carelessness, dishonesty, disregard, narcissism, cultural norms, and much more.

Perhaps a better question to ask is: why do we struggle to be honest with ourselves and with others? Many reasons: we are scared, we fear rejection, we fear our past and our pain and we conveniently distract ourselves. I know I did.

I would be in agreed-upon monogamous relationships, yet I would feel so restricted and I would seek women outside of the relationship—being unfaithful and being secretive about it, whether through prostitution or one-night stands. I felt such relief and such guilt at the same time. The time to take ownership of this was coming, and it was necessary for my eventual transformation.

The major catalyst for my propulsion into self was, of course, an intimate relationship. It was here that my transformation, repositioning of my life and masculinity, and full acceptance of my darkness began.

When she discovered the truth of my unfaithful behavior, our romance unraveled. I did not even have the courage to tell her first. Her intuition, recognition of patterns in my behavior, my distance, my aggression, and posturing told her enough. From here, I witnessed someone who I sincerely cared for and loved devastated and traumatized by my dishonesty and actions. I observed her whole world crumble because of my actions. 

This was intense for me to say the least. My whole life quite literally flashed before my eyes. Shame and repressed trauma rose to the surface of my awareness and I realized that I had to change. I realized that I actually wanted to “be caught,” to free myself of this burden.

I remember the day as if it were yesterday. I left my phone in the car as she dropped me off to help an elderly couple. She had a hunch to look through my phone and found some old emails from a sex-dating website. I had never met with these particular women. I was just talking with them, thinking I needed the adrenaline rush and dopamine hit of the anticipation and the pursuit. 

She picked me up and my heart sank. I knew what had happened and from there, an immense journey unwound. More lies before truth, trying to protect myself, and her. But I couldn’t. It was time. 

And unfortunately, it had to come with so much collateral damage and pain inflicted on another…

As men, we want clarity and verticality and we can only embody this when we are clear within ourselves. Every time I was close with a woman, fear would surface and I would be with other women in whatever way possible to give me inner relief. I wanted the safety of intimacy and partnership, yet I could not be with just one woman. 

Some would say that this is a natural biological function for both men and women to yearn to be physically intimate or sexual with multiple people, and there is truth to this. But what was primarily driving me was not natural, healthy biological urges—it was deep fear. I know this unequivocally because when I consciously took myself through certain processes of discovery, these burdens were lifted, my behavior changed, my foundations shifted, and I was liberated.

Having witnessed such toxic and unhealthy relationships growing up, the subtle associations I made with relationships were disconnected. I wanted intimacy (something I knew two people could grow together, impacting the world and each other—sacred union), but my body (traumatized from what it was holding on to) was a massive, “No!”

Observing her pain was a breakthrough for me. I had two choices:

Go deep into all of this, unpack the layers, and get f*cking real with who I was and what I had become, how I treated others, and myself—or remain in ignorance.

She was graceful; she also chose not to come from previous conditioning and realized that there was potential healing in the situation, but only to a certain extent. It was too painful for both of us and we tried it all. I stopped my businesses and threw it all into healing. Councilors, therapists, trauma specialists. We attempted to make it work. There were times where it was intense. Her rage came through in various ways. I developed a capacity to hold and step into healthy boundaries (as did she) not in the way I had before. This extended experience gave me tools in real-time.

It wasn’t, “Oh, I’ll show up differently in the next relationship (where the other person hasn’t experienced my volatility, hurt, and darkness).”

No, I was (we were) doing this in real-time and it wasn’t easy. On edge constantly, she would ask, “Why, why, why?” She had every right to ask for what she needed. This is true, and she would ask for details…

I do not recommend you go there. We think we need to know more than we actually have to. This can cause serious and unnecessary pain. Be mindful of what you need to know in order to heal. In short, we ended the union after a few months of attempting to make it work. I knew we were different people and I honored that. I knew she was not for me and I was not for her. 

In the final part, I continue the story, further unpack the transformations I experienced, and how I finally broke free of my pain, my fear of freedom and commitment (two core fears men hold deeply in their bodies), and became the person I am today.

What part of my story so far has been applicable to your life? Please share in the comments and follow me on Elephant for a heads-up on part four.


Read 2 Comments and Reply

Read 2 comments and reply

Top Contributors Latest

Stefanos Sifandos  |  Contribution: 100

author: Stefanos Sifandos

Image: @muhammedsalah_/Instagram

Editor: Khara-Jade Warren