For the past five years, my professional focus has been on conducting 'relationship training' workshops, primarily for heterosexual individuals. The objective has always been to teach principles and skills for building healthy and intimate relationships.

So, when a lesbian colleague approached me about a year ago to extend these workshops to the gay population, I felt ready to venture into what was, for me, uncharted territory.

During one workshop with eight gay men, the issue of anonymous sex quickly became a focal point.

Several participants expressed concern about whether engaging in anonymous sex aligned with what they were ultimately after. Then the focus shifted to what they’re needing and were missing in their relationships and their lives. I was aware all the while, that the space felt safe enough for them to begin opening and sharing in a way they never did with anyone else before.

There was a point in the process when I had an epiphany. I was in a group of men, most of whom, were in recovery, hadn’t ever been in a nourishing or intimate relationships, that they were struggling all their lives with the residual effects from childhood trauma, which certainly limited their ability to connect with anyone and played out in their adult relationships.

The epiphany I had was that they weren’t able to and didn’t know how to connect and that anonymous sex or sexually based relationships was a for them to make up for what was missing and found a way to connect with another person in a way that felt natural, safe, exciting and seemingly intimate, being physically naked and, having sex that was void of emotional intimacy or deep connection.

Some described their experiences with anonymous sex as liberating, self-affirming, balancing, and satisfying, feeling their lives had been enhanced by it. Others confessed to a 'love-hate' relationship with the practice and were specifically seeking guidance.

There was a consensus in the group that anonymous sex really wasn’t healthy, nourishing or feeding any of them and intensified their underlying worthlessness and alienation. While it provided physical contact and orgasms — a temporary fix that was readily available and took the edge off, it proved unsatisfying in the end.

The fundamental need for emotional connection and intimacy remained unmet, leaving them with a sense of emptiness once the encounter was over. It wasn't delivering what many ultimately yearned for: a relationship that combined sex and intimacy, that provided the safety to be themselves with each other, honest, real and vulnerable, like they were when opening up in the group.

Exploring the roots of their involvement with anonymous sex, many traced it back to years spent in shame and secrecy about their sexuality. This was compounded by the 'normalization' and, at times, glorification of anonymous sex within parts of the gay community. For some, having sex with anyone they chose, anywhere, and as often as they wished, became a way to celebrate their sexuality and newfound freedom—a powerful act of rebellion and self-acceptance.

Given that liberation was a unifying principle of the gay liberation movement, exercising freedom in this manner understandably served to invoke pride and strengthen identity. However, it became apparent that this focus could lead to an overemphasis on sexual freedom, sometimes at the expense of other equally or more important values, such as the quality of relationships and the capacity for deep intimacy.


We discussed the danger of simplistically equating anonymous sex with freedom, as such encounters carry other, often unacknowledged, implications. True freedom, we explored, might lie more in our ability to experience our desires without impulsively acting on them, to assess situations, and to act in our own best long-term interests. The power to choose how to act, considering the consequences for us and our relationships, is where authentic freedom resides. When anonymous sex becomes an integral part of one's lifestyle simply because one is 'free' to make it so, the definition of freedom can become distorted, as if it exists in a vacuum devoid of emotional context.

Many who practiced anonymous sex described acting on impulse, drawn by its easy availability and immediate pleasure. Crucial questions often went unasked: 'Does it matter if I know or care about this person?' 'Do I feel better about myself afterwards?' 'Do I feel more connected to others, or more worthless and isolated?' To truly understand the role anonymous sex plays in one's life, these questions need to be explored, whether with partners, friends, or therapists.

This led to the realization that anonymous sex might often be more about unacknowledged need than about genuine freedom. I once heard a man quip, "Gay men have stronger libidos. We go down at the drop of a zipper." While the relative strength of libido isn't the core issue, his comment highlighted how basic our sexual needs are. However, our emotional needs are at least as powerful, if not more so. Many of these men seemed disconnected from the intensity of their own unmet emotional needs. Undeniably, the pain and the urgency to relieve it are most acute when both emotional and sexual needs are denied.

As the men shared more openly, it became clear that for some, sex had begun to serve so many purposes that it resembled an addictive pattern. For many who engage in anonymous sex, it can become a vicious cycle.

Joe shared, "I look for sex when I feel like, 'Who would want me?' Then I get into a sexual situation, and I'm suddenly wanted."

Tom elaborated, "I use anonymous sex to get validation, to feel a connection. It's when my self-esteem is low that I'm most apt to act out sexually. Today was a good example. Driving up the freeway, I was noticing the rest stops, checking how many guys were pulling off, looking for action. When I'm isolating from friends, going to the park is an answer. It feels like the only way I can connect with another human being when I'm feeling bad about myself. The only one I'll let into my space is someone with whom I can have anonymous sex. At one time, it was nothing for me to go off at lunchtime for a couple of hours and have two or three orgasms with two or three different guys, then stop and do it again on my way home."

Bill confessed, "When I'm exhausted, it's a struggle not to get sex. All the thinking in the world isn't going to keep me from doing it. I wish I could convince myself to stop. Once the idea pops into my mind..." Jack reflected, "I was motivated by excitement, deviance. I felt totally alienated from society. I was far too sensitive to engage in anonymous sex on an ongoing basis; it was too humiliating and hurtful. I always felt worse afterwards. The lengths I went to get sex that wasn't part of a meaningful relationship did nothing but kill time. It was never as good as my fantasies."


Summary

This exploration reveals that the allure of anonymous sex can sometimes mask a profound hunger for connection, a hunger that, if unaddressed, perpetuates a cycle of quick fixes and deeper isolation. The challenge, and indeed the path to a more integrated freedom, lies in learning to cultivate the self- awareness and skills necessary to build healthy nourishing relationships, ideally before sex enters the equation. It’s about recognizing that our deepest liberation comes not just from the freedom to act, but from the wisdom to choose actions that nourish our whole selves—sexually, emotionally, and ​relationally.