A friend of mine texted me to say they feared that my reputation was getting “kinda bad”, and wanted to help me salvage it. I shared that fear. We met up to chat that same day.

I was unsurprised to hear that the bad reputation I was accumulating was due to my It's hard to define this precisely. The same behaviors can be transgressive or not, depending on context. "Touchy and forward" is a decent description of what we mean, but ultimately it's about vibes, and I'll trust you, reader, to vibe with my friend and me as we discuss. I’ve been cultivating that somewhat purposefully, as a new thing that I’m experimenting with. Like many nerdy guys, I’ve spent much of my life in a state of sexual repression, fearing the possibility of ever making a woman uncomfortable. I got so good at controlling myself that I forgot how to notice my impulses. I went to SlutCon last year, and one of my takeaways was that it’s ok to express desire.

A big takeaway,” Ari shared later, “is that I can ask for so much more than I habitually ask for, and it’s totally fine.” SF Standard

It was a good lesson. It moved me out of the failure mode I’d been sitting in for most of my life. Unfortunately, that meant I moved into new failure modes! I selected I won't name them here, but if you run in my circles, you can probably make some decent guesses as to whom I'm talking about. who express a lot of sexual desire and have a lot of sex and seem pretty happy about this, as role models while I explored this new space. Predictably, as I mimicked their behavior, I ran into some of the same reputational consequences they face, exacerbated because in this unfamiliar domain, I lacked their skill and comfort. It turns out that when you stop worrying about making women uncomfortable, you start making women uncomfortable. As my friend put it, “that anxiety was protective”. SlutCon is a very particular environment, where the women are selected for openness to approaches by men, and even more open than usual due to the nature of the container. It does teach valuable lessons, but it’s important to be careful when generalizing to the rest of life.

My friend pointed out that I was failing to attune to the women I was hitting on and read their signals of disinterest. Yeah. Oof. I was sad to realize that, because I thought I was pretty decent at Perhaps I still am when I'm not getting in my own way, but at any rate I can't rely on my attunement skill for the time being. Without improving my underlying attunement, I just traded the direction of my errors. Instead of overlooking signs of positive interest, I was now overlooking signs of disinterest. That’s much more socially dangerous. My friend warned me that if I continued down this path, I could find myself ostracized by my community.

I tend to grow by way of alternating corrections, rather than incremental change. Once I realized the error of repression, I swung into transgression to figure out where the boundaries are. This conversation with my friend, along with some other recent strong feedback, was a sign that I’ve gone too far, and it’s time to swing back towards a middle ground.

Mimetic Desire

In my social circle the Slutcloud, the part of my social circle that talks the most openly about sex, the hottest men who have the most sex share certain proclivities, or at least give the impression that they do. They’re agressively dominant, sadistic, and very horny. The women who form the core of the Slutcloud are into these traits, expressing the complement: submissive, masochistic, and also very horny. There are cool parties that many of my friends attend, where the vetting process includes looking for men who are genuinely into realistic rape fantasies. I felt (and still feel) FOMO about hookup culture and sex parties; since I was a teenager, I’ve had an insecurity that My friend correctly challenged this perception. It's easy to assume offscreen fun that isn't actually happening; indeed, people often assume that I'm having lots of sex, when in fact that's far from the case. I suspect this type of insecurity is fairly common. Unfortunately, that knowledge is only so helpful in comforting my anxious id. and I’m not a welcome participant. In this milieu, as men so often do with feminine attention and social acceptance on the line, I started warping myself to fit in.

It’s not really me though. When I’m not getting in my head about being like the cool guys, I like collaborating with people to satisfy desires, and causing pleasure rather than pain, and honestly I’m just not that horny. I’ve mentioned that to a few of my friends, to set their assumptions straight: I have horny vibes, and I’m fascinated by sexuality, but I’m not actually that interested in sex. This showed through my behavior as I explored the bounds of sexual conduct, and the mismatch made the vibe creepier. As my friend put it, I wasn’t acting “from the gut”, and women notice that sort of thing!

I can still feel the worry about not having the “right” preferences. I quite like many of the women and men of the Slutcloud, and if they’re uninterested in me because I don’t share their sexual tastes, I’ll be sad about that. As always though, I need to be true to myself and express my truth, and trust the flow of the universe to filter me into the right context.

Before his death, Rabbi Zusya said “In the coming world, they will not ask me: ‘Why were you not Moses?’ They will ask me: ‘Why were you not Zusya?’”

Sexual Agency

I do want to ever get laid. It’s not one of my highest priorities, but it does hold some importance. I can feel myself getting grumpy when I go too long without sex. Now, I have had sex without being sexually transgressive, but… it frustrates me that sex hasn’t felt like something I can pursue. When it’s happened, it’s been the result of a woman making her interest extremely obvious, and me going along with it in various states of amazement that I got so lucky. My foray into forwardness was an attempt to take the reins, so that sex would be something I can make happen instead of something that happens to me.

My understanding is that the conventional pathway for making sex happen is dates. I don’t understand dates. I’m trying to learn, with some theoretical success thanks to resources like the Slutstack, but it’s slow going. It remains the case that in my life, I’ve had more serious relationships (3) than First Dates (2). I especially don’t understand the mechanisms by which a date leads to sex. I hear discourse about whether to fuck on the first date and find myself intuitively baffled that it’s even a possibility to consider.

Far more than sex, I’m looking for love. I don’t know how to take agency in seeking that either (see above regarding dates). My strategy historically has been 1) make friends and cultivate community 2) ??? 3) find myself in love. I was actually pretty agentic about pursuing my most recent romantic relationship, but only after several years of platonic friendship. That agency also caused some problems. It’s a tried and true strategy, to be sure! I’ve gotten into some wonderful relationships this way, and I’m continuing to lean hard into the first step, creating the surface area for serendipity. However, it’s also true that historically this strategy has resulted in me going years between romances, and I don’t want to wait. I’m lonely and yearning, and I’m not getting any younger. Perhaps I’ll eventually find that the process simply can’t be rushed, but I’m not ready to embrace learned helplessness yet. I want to try a few more yang approaches to finding love before I decide to go (back to) full yin.

I Don’t Give A Damn ‘Bout My Reputation?

Well, let’s be clear: I very much give a damn about my reputation. My community is important to me, and I would be devastated by ostracism. That said, I basically buy the theory that the goal ought to be maximizing fans rather than minimizing haters:

Chris Lakin’s graph of being liked vs. disliked when secure vs. insecure

I’ve accepted that by putting myself out there and refusing to minimize my identity presentation, I’ll inevitably cause some people to dislike me. I’m generally ok with that. However, my foray into sexual transgressiveness seems to have had no real benefits! It was somewhat fun to put on a new persona and explore boundaries, but I had no additional sex beyond what I would’ve likely had regardless, and no one seems to have been impressed by my boldness. I was acting not from a place of security about my internal drive, but rather insecurity about my community approval and doubt about my self-knowledge.

What Has Worked Well

I have made some sexual-transgression-adjacent bold moves that were met with positive results and felt good. For instance:

  • I sometimes ask people if they want to cuddle. Quite often, the answer is yes!
  • I was cuddling with a woman at a party (by way of the previous point) who I had crossed paths with a couple times before, but hadn’t previously talked with in depth. Earlier in the night, there had been a conversation about her thoughts on being asked out, and she had pretty mixed feelings. I asked her on a date anyway. She declined, saying she wanted to That worked fine for me, since that's my usual mode and I was stepping out of my comfort zone by asking so soon. I had gathered up all my smoothness for the initial ask, and stuttered somewhat explaining that. Regardless, when she texted me the next day to give me her number, she said she had fun with me at the party and "I maintain you have good vibes". but said she liked the way I asked.
  • At the end of a party, I was hugging a friend goodbye and felt a strong urge to kiss them. I looked away, made eye contact again, and said “wow, I really want to kiss you”. They said “you can kiss me on the forehead”, which I did.
  • I made this Glosso post, and a few of my friends sent me nudes as a result.

Glosso post titled “I like getting nudes from my friends”

It’s worth thinking about what separates these from the transgressive moves that damaged my reputation and feel like clumsy mistakes instead of brave achievements in my memory. Some thoughts:

  • Authenticity, “from the gut”. All of these actions were driven by clear internal desire, rather than a sense that I ought to be exploring and pushing my comfort zone. I love cuddling! Receiving nudes is delightful! I like this woman and want to spend more time with her! (The timing of asking her out was deliberate comfort zone expansion, and I think that’s why it was the most awkward part.)
  • Existing rapport. These moves were mostly with people who already had a history of friendly interactions with me (establishing my weirdness as non-threatening) and whom I’d had opportunity to learn how to read. In the exception where I invited a woman to cuddle without much prior conversation, we had already established that we had both attended SlutCon (shared culture of openness), and her vibe was strongly receptive.
  • Easy outs. In asking to cuddle or go on a date, saying no is a clearly-signposted option (and the way I ask conveys the true fact that I’m ok with it). When I said I wanted to kiss my friend, looking away showed shyness, so my vibe was vulnerable rather than pushy (and also, I already trusted this friend to hold their boundaries). The Glosso post was probably the most transgressive of these moves, but wasn’t directed at anyone in particular; those who were interested could opt in, and those who weren’t could simply ignore it.
At my dessert nights, I often hug my guests hello/goodbye. I wasn't sure if my friend, who's younger than I am and has turned me down for a date in the past, wanted a hug, so I avoided putting them in the position of refusing one. When they were leaving, they said "Don't think I didn't notice that you hugged everyone but me when they arrived." I've worried about this exact situation, but I didn't expect to actually get called out for it! I hugged them goodbye, of course.

Now What?

I felt a strange sense of relief as my friend tore apart my ego defenses, as something in me relaxed into place. Figuring out who I am is a strangely difficult ongoing project. This experiment with sexual transgression was one step on the journey of trying things to see what works, but this one didn’t work for me. With this strong external nudge from my friend, I have a clear internal Schelling point to declare the experiment over and move on to finding an approach that’s more true to myself. As I processed these reflections, I imagined myself in a couple of scenarios saying something to the effect of “nah, I’m not really feeling it” about some sexual activity, and I felt my shoulders unclench. One of my SlutCon takeaways was that it’s ok to express desire, yes, but another was that emotional connection and gradual escalation are important to me, and I’ll do well to remember that.

I think it’s wise to retreat to a state of apparent asexuality temporarily, as I pause and assess. It’s safe, and right now, safety is what I need. Long-term, the right answer isn’t to go back to my previous state of supressing my desire. That frustrated me, and likely also left some women dissapointed by my apparent lack of interest. Any strategy that involves constant denial of what I want for the sake of others is ultimately doomed psychologically. I still want to figure out how to take agency in looking for sex and love. I’m sure I’ll continue to make mistakes as I flounder around trying new things, but at least they’ll be novel ones.

The only failed experiment is one you don’t learn from. There have been some negative consequences to this one, but I have learned about myself and my social context! I’m excited to move forward with this knowledge and continue clarifying who I am and what shape of life is right for me. I’m very grateful that I have such good friends, wise and caring enough to have these tough conversations that nudge me onto better paths.