The other day, someone told me, “I can’t imagine you ever being awkward with people.” And I thought, oh God, yes, say it to me again, again, put it in my veins. Tell me I’m a natural performer. There are no sweeter words.

Because of course the absolute opposite is true. I’ve tried so hard to learn how to connect with people. It’s all I ever wanted, for so long. I can still remember the pain of my youth, when the brightness of my experience felt like a wasted gift, a rude excess, without anyone to meet me in it. And I remember how many years of deliberate practice were required to secure routine pleasant interactions with my fellow human beings. I was born without social awareness, and I installed mine bit by bit.

Looking back, it’s clear to me now that my increase in social skill wasn’t linear, like building a little more strength with every trip to the gym. Instead, I had six different paradigms of connection — six entirely different ideas of how to approach people — that I moved through on the way to my current method.

As a child, I was abrasive and abrupt, excitable and sensitive. Interacting with me was exhausting. And my position in the hierarchy reflected it. I was probably the most severely bullied kid at my school, because I was one social notch above children who were so pitiable it would be rude to mock them.

In early adolescence, not much had changed. My closest friends were the hosts of This American Life, which I discovered through a webcomic about video games. On first listen, I recognized that the adults on that show were unlike me. They were witty and urbane, confident but self-deprecating. And, since I adored them, I figured that to be adored, I should be like them. Thus, I determined that I would fashion myself into an interesting person to listen to, and this remained my approach throughout most of my undergraduate education.

Thus, in my teens, during/after a spell of playing the ukulele in public to attract attention, I:

• Memorized poetry and read difficult modernist novels

• Got good at telling dramatic stories about my life

• Developed opinions about scholarly subjects, like Roland Barthes, Werner Herzog, and so on

In essence, I became an example of obnoxious precocity, a heartfelt young wordcel.

This earned me a bit of approval. But the approval was polarized. My act only worked on those who valued a particular kind of cultural intelligence — everyone else just found it tiring. And even when it worked, which it did chiefly on campus, it was distancing. There was a presentational quality to my interactions, which limited the possibility of real dialogue. At the time, I could see that I wasn’t yet one of the gang, but couldn’t see why. I was demonstrating my erudition: surely that was enough to be inducted into the ranks of the socially accepted?

The limits of my approach, and how to move beyond it, only became clear when I worked in restaurants.

After becoming NPR-ish in college, I went insane for a bit. Like, real mental illness, dark night of the soul, wandering the streets muttering to myself, constant suicidal urges.

When I recovered, I found myself working as a busboy at a high-end pizza restaurant, where I was being considered for promotion to the rank of bartender. I’d become capable at making coffee and cocktails, but my social skills were considered unacceptably poor. I overheard one of the bartenders, who felt I shouldn’t be promoted, discussing me with the manager: “He talks in paragraphs,” was the complaint.

Aware of my deficits, I started studying the servers who were socially admired. And I started noticing that they operated in a completely different paradigm from me. Some of the servers, who were decent, did what I did — they presented a fixed role, a plausible bit, like “extravagantly gay man with quips,” or “cheerful country girl.” But the really good servers had flexibility. They would figure out what social game the other person wanted to play, and then they would play it with them.

If their tables ordered in a brusque and direct fashion, they became efficient and stoic in response. If their tables wanted to flirt and banter, the servers would animatedly yes-and whatever came at them. They were responsive — they weren’t looking to shore up a preexisting identity, so much as they were simply open to play.

Although adopting this approach required practice, I instantly recognized it as superior, and took to it devotedly. After a year of this, my manager said to me: “you’re never going to be my top salesperson. But you make people ridiculously comfortable.” It can be easy to change your personality when it’s organized around achieving a goal, and you realize your previous strategy isn’t going to work. Also, restaurants are a great arena for trying on a new persona, given that every new table is another opportunity for novel behavior.

I started feeling like I was pretty charming, and this was true, relative to my standards. However, when I moved to a restaurant with more seasoned servers, I learned that I was still a beginner.

I transitioned into a fancier, nicer restaurant, in a cooler neighborhood, where I was, again, the awkward kid. I was now surrounded by real adults who were really urbane and charming — career servers who had spent over a decade refining their social procedure.

There was one in particular who captivated me. Compared to the others, he was messy. He forgot orders, recommended weird pairings, and sold tables on entrees that the restaurant had stopped serving a month ago. Nevertheless, everyone loved him because of his incredible social skills.

But they were weird incredible social skills. He constantly said things that didn’t make any sense. “Let’s go home,” he’d say, as a greeting. “Lovely ball,” he’d say, as an assessment of quality. There were dozens of other catchphrases and odd habits. Somehow it worked. I watched everyone adore him for some time, me included, while feeling incomprehension re: how this effect was being achieved. What I started to realize was that his surreal quirkiness was sending out an unspoken message, something like: “I’m not a real server. This isn’t a real restaurant. All of these social roles we’re inhabiting are just fictions. We can all just relax.” His odd, uncontained manner gave permission for everyone else to escape containment in a collective jailbreak.

I adopted this attitude in my own way, tacking on bits of benign strangeness to my interactions. Whenever I offered water to tables, I said it in an odd, skeptical way, as if I’d just become lucid in a dream. “Hi…,” I said, while making direct eye contact. “Can I get you some… water?” I’m not exaggerating when I say that about 95% of my tables loved this instantly. By being awkward on purpose, I became their relatable comrade, rather than an impersonal representative of a snobby establishment.

Previously, I’d thought there were two choices you had with a social script: reject it, or go along with it. But I started developing an instinct for a third choice: how to take the other person sideways, into the weirdness of open possibility, where it’s not clear how anyone should feel, and there are no requirements.

For example, I once spilled a bottle of olive oil onto a woman’s lap. She happened to be wearing an exquisite blue designer suit. I looked her in the eye, and I could recognize that she was about to be angry. A reaction was forming on her brow, like a looming cloud. In the brief moment before thunder struck, I said: “Sorry, I was just distracted… by how special you are.” She paused, startled again. Then she broke into a huge smile, laughed uproariously, and grabbed my hand with both of hers. We looked at each other for a moment, silently, and the rest of the table also watched, unsure of what to think. “Send us the dry cleaning bill?” I said. “Sure thing,” she said. I nodded and ducked out, leaving it there. It was someone else’s table, and the server reported that she received an unusually large tip.

This penchant is still a large part of my conversational habits. Much of what I say, in casual chit-chat, is directed towards loosening the grip, rather than conveying anything in particular. This inspired a blog from my wife about how some people communicate in order to exchange facts, and some communicate in order to find connection:

This didn’t click as an explicit model for me until recently. What did it was hearing my husband, again and again, say things to people that made me cringe because to me they sounded hostile or disingenuous. And again and again, I was confused when people’s reactions to him were almost universally positive. Clearly, the issue was that I was lacking some essential piece of human software, not his sense of propriety. Now, I’m not a total dolt — I’m familiar with the classic wisdom that a large proportion of communication is non-verbal. I can read body language quite well, thanks to deliberate study as a poker player, and I know to smile, send out friendly vibes, mirror the other person, all the things you can read in a book. But until I watched Sasha in action, and we tried to analyze my hang-ups, it really didn’t sink in for me just how much less important what you say is, to most people, than how you say it.

It is gratifying to me that this lesson propagated through space and time from an Italian restaurant a decade ago to a recent Substack post.

However, after I learned this trick, there were still a couple of major updates yet to go.

I quit fine dining to be a roving freelance journalist, then achieved my childhood dream of becoming a published author. It did not make me happy.

I then entered the classic California pipeline: when worldly pleasures fail you, attempt to locate the happiness without conditions. I became a self-therapy and meditation nerd, and, as a result, I achieved a much greater level of embodiment. I realized that I’d been stuck in my head for my whole life — that this is not a figure of speech, but a real description of how your subjectivity is very different when you’re uncomfortable with emotion, and living behind the sensory filter created by a rigid self-concept.

Bam! I was plunked into the vivid depth of bodily expression. There was so much I’d missed before. Though I was verbally skilled from my restaurant training, sometimes my timing was off, because of all the delicate non-verbal signs hidden from me. It was not unlike a colorblind person, unaware of their condition, suddenly seeing the whole rainbow.

There were these new, subtle flavors of human presence in front of me, like:

• The bitter-edged weariness of a person who feels underpraised

• The wary stiffness of a man in charge who feels insecure

• The speed of a nervous intellectual trying to dance around their emotions

• The languid tones of someone presenting themselves as a sexual option

• The leonine nonchalance of real confidence

I started seeing new subtleties in people I’d known for years. It was like I got to meet everyone again.

Before this, I’d interacted with people who seemed psychic. They could pick up on delicate undercurrents of my state that I wasn’t even trying to communicate, or befriend me instantaneously by giving me exactly the kind of attention I wanted. And now I thought: oh, this is how you become psychic. You just fucking look at what is happening on the faces and bodies of other people.

With this new perspective, connection felt a lot more like dancing. If I stopped to think about the information I was getting through body language in real time, then my communication became leaden. But if I simply reacted, from a state of fascinated absorption with the physical data in front of me, somehow it typically worked out okay.

This could have been where it ended, but Twitter, that beautiful scorpion, changed the trajectory of my life again.

Flash forward to 2021. I’d started working as a writing coach during the pandemic. I didn’t have much coaching experience, so I didn’t yet know what my style was. And I was living in the desert in a decaying marriage, which made me feel experimental. “How did I get here” is a question that sometimes enables a mood of “and where else could I go?”

I stumbled across a tweet by Tyler Alterman, talking about how he had managed to get autists to successfully do energy healing simply by earnestly pretending to be energy healers. And I thought, “alright, fuck it, I’m going to pretend I can heal people with my energy.” I had no illusions about the truth of this, but I wanted to take it on as a useful fiction, to see what would happen.

I thought about people I knew with an energy I’d described as healing. There was something they had in common, maybe. A nonjudgmental, velvety openness, an alertness without a sense of problem. Perhaps I could try that.

I’ll always remember the first call I took in this mode. I slipped into a groove that I was familiar with from Zen meditation, a place of spacious openness, luminous awareness. Rather than trying to get to the bottom of the issue, I just focused on being in that state with my interlocutor.

They had a moment of tremendous emotional catharsis, complete with full-body sobbing, and thanked me for opening their heart. And I was like, for opening what now? I didn’t do anything except relax and gaze softly and ask a few questions. This doesn’t make any sense.

After a few similar occurrences happened, I learned a couple of things that seem, in retrospect, obvious:

• A large-ish amount of the action of therapy/coaching is simply having nervous system capacity for someone in distress.

• Many people are desperate to be listened to because so few people listen, so if you go around your life in a state of presence and openness, you will be treated like an oasis in the desert.

• If you meditate long enough to react to the world with loving gratitude, people can really feel that.

It seemed like a prank, overall. Connection was impossibly scarce when I was a kid. Then, it became something I could obtain through a delicate social dance. But after this paradigm shift, I learned that if I just threw myself open, other people would do all the work.

Sure: it took me a lot of intentional self-renovation to equip myself to do this trick. But once I did, it was easy. And potent. I started hearing phrases like this a lot: “I don’t know why I just told you that, I’ve never told that to anybody.” It was shocking to find instant intimacy with what felt like anyone, anywhere — whether it was the schizophrenic son of a cactus store owner, or, after I got a divorce, a first date with someone I didn’t even have that much in common with.

But there are upsides and downsides of making your whole life into a connection-fest.

There are two reactions that one could have to the previous section. “Wow, that’s cool, how he developed the ability to create a lot of deep connections in this lonely world.” And: “that is a weird and creepy thing to want, sounds kind of vampiric.” I believe that both reactions are correct in some proportion.

Here is the thing about going around the world in a state of emotional openness and presence. Many people are hungry for that kind of attention. They might dream of getting it from a parent, or a mentor, or a lover, but might never receive it. Maybe never in their lives. And if you just walk up and give it to them, for free — but you aren’t actually interested in a deep relationship — then they might, rightfully, feel manipulated, or at least confused. You are writing them emotional checks you can’t cash.

Because… what? You want more connection? Why do you need that, right now? Can’t you be comfortable on your own? These are questions I started asking myself when I realized that my whole life was becoming a therapy session. And I also realized that, even in a therapeutic conversation, going right for maximum emotional connection was rarely the most productive move.

Around this time, I’d started dating my now-wife, and we decided to be monogamous. In a classic moment of Cate candor, she said to me, without a hint of anger or judgement, something like: “it seems like a lot of women have crushes on you. I don’t think you have bad intentions, but this must be a product of something you’re doing.” And, in fact, it was; I was going around dangling the possibility of emotional connection indiscriminately, ignoring the fact that it’s entirely reasonable to interpret this as flirtation.

So I resolved to moderate my approach, to slow the whole gooey business down. I settled on a goal: to consider connection as a dial going from 0-10, and to be comfortable with any setting on that dial. And, rather than always pushing things in the direction of connection, I resolved to follow my conversational partner’s lead. Someone wants to have a four-hour bonding conversation at this house party? Sure, let’s do it. Someone wants to say “let’s get it” and literally nothing more before we spar in jiu-jitsu class? I also want to interact in that mode, and to consider each human interaction equally informative and worthy of attention.

I chilled out. And by that, I mean I:

• Meditated for hours in float tanks, to train myself to enjoy deep presence completely on my own

• Read a bunch of stuff about anxious attachment, and tried to nudge myself in the direction of secure

• Tried to deeply accept feelings of solitude, which led to a life-defining mystical experience

It’s been a couple of years since I set my personal goal, and I’ve mostly achieved it. I routinely have interactions that are achingly rich with emotion, but also conversations that skip merrily on the shining surface of pleasantry. I’m told that I can come off as standoffish, and sometimes a little bit intimidating, which is welcome news.

Perhaps now, I am finally socially normal.

Thank you to my darling Cate Hall for input on this piece. Credit for the image goes to Dan Allison.