235A. DatingOS: Leveling Up for Dating
Your "Level" is the most important determinant of dating success. Here I explain what that means, how to raise your level, and why advice from "dating coaches" rarely works.
I recently wrote about Bumble’s planned move to introduce AI assistance into their dating app. There I explained that using AI as a crutch will reduce your ability to level up, and that leveling up is the most important thing you can do when dating. Due to the complexity of that concept, I didn’t really attempt to define or explain that, which might have left my readers a bit puzzled as to what I meant. Here I remedy that, but it requires its own article since its a very complex subject.
The idea that you can “level up” in life will make intuitive sense to any gamer. Usually they are leveling up their avatars in games, but not leveling up themselves. In 2010 I wrote Third Tier of Game Development, and I still consider it the most important paper I’ve ever written. That’s why it is paper #1 on my substack. Every paper I write connects back to this one in some way.
Not only did Third Tier predict some of the greatest challenges we face today, but it introduced the concept of Trans Realistic Experience (TRE). The idea here is that in the future, when we will use AI to augment people (instead of this ruinous attempt to replace people), people will play games where they gain experience and level up over time. Not the avatar of the player, the actual player.
Humans are pretty amazing creatures. They can learn an almost infinite number of skills, and the more they practice a skill the more it levels up. Back in 2006 I had the chance to meet Todd Howard, the guy over at Bethesda. I took the opportunity to lampoon his new game Oblivion in front of about 50 members of the press pool by pointing out that I had put a rock on my keyboard and came back a couple days later and I was max level in Oblivion.
I wasn’t embarrassing Todd for being short or having Main Character Syndrome, I was giving him a hard time because he has a very simplistic view of what experience is and how critical it is to human development. If you’ve tried Starfield, you can see this hasn’t changed much since 2006. Perhaps the greatest superpower that humans have isn’t racial diversity, cultural diversity, or identity diversity. It’s skill diversity. For productivity purposes, matching the right person with the right skills to the right job is perhaps the greatest technology you can develop. That’s what Third Tier was about, and the world is suffering because the big Tech Bros decided to pass on this tech in lieu of using AI to replace humans entirely.
Groundhog Day
In the 1993 movie Groundhog Day the main character (played by Bill Murray) gets caught in a time loop. Every day he wakes up again on the same day, but retains all memories. He could do the same thing over and over, like my Oblivion avatar getting XP for throwing fireballs at a wall. Instead, he learns all sorts of skills like how to speak French and to play the piano expertly.
When I talked to 250,000 women between 2010 and 2020 for the purpose of developing the field of Dating Economics, I could have done the same thing with every person I talked to. But that’s not how humans learn. They learn by trying new things and figuring out what works and what doesn’t. The problem here is that every person you talk to is different and what might work with one person might not work with another. That’s actually a good thing, because the key thing to learn here isn’t how to say the right thing, but to expand the options you have in any situation.
In well designed role playing games (RPGs) that encourage replayability you may have a dialogue with a non-player character (NPC) where you can reply one of three or four ways. The default option, the one everyone can do, is usually the worst possible choice. The other options require expertise in some skill. If you don’t have any of those skills, you are kind of screwed with the Default Choice. On a date, that’s the option that doesn’t lead to a second date, or an invite to the other person’s house.
If we had access to AI that could give us TRE then we could become experts at accelerated rates, kind of like how in The Matrix people can just download new skills. You’d still have to learn them, but the total time required would be greatly reduced. You could do this while playing and end up a real life expert at something as a side effect of having a great time.
My concern about having an AI do the heavy lifting for you in Bumble 2.0 is that this would block you from developing XP and leave you crippled socially. Unless you plan on having AI do your whole relationship for you, at some point you have to fly solo. If you don’t know how to, you will crash.
The Two Skills that Dating Losers Don’t Have
Here when I say “Dating Loser” I mean someone who goes on dates but doesn’t get what they want from them. All those single “dating experts” trying to tell you how to land a relationship? Dating losers. Not the best people to be taking advice from. They often will teach you how to find fault in other people, which is also teaching you to lack responsibility. That’s a huge XP penalty.
So what are the two most useful skills? How to act interesting? How to flash cash? How to dress seductively? How to date safely? [useful, but not the top 2] How to have 5 suitors on rotation? Blech no. How to space out your text replies to not sound too available or eager? How to apply make-up? Big no. How to tactically neg a person to get them off balance? You’ve all heard this sort of advice and (with the exception of safety tips) it’s mostly garbage.
There is a third skill, but it’s by far the hardest: Listening. It will take me all three papers in this series to explain how to do it effectively. So I will wrap up the third paper by explaining this elusive skill.
Speech
Having grown up feral I was pretty good at talking to animals, but not to humans. Being the school freak meant I had a lot of adverse interactions with people growing up. This wasn’t a problem on my military career path, but when I hit age 18 and decided to reject militarism for pacifism, I was in new territory. I decided to create, not destroy, and enrolled in nursing school. This was an environment that would force me to learn compassion and empathy.
My first big hurdle was Speech class. It was a prerequisite course before one could start clinicals. I had no idea how terrifying this class would end up being. Getting up in front of a crowd and talking on a subject for 5 minutes would inflict panic. It would have been so tempting to just drop out, but that meant failing at nursing. So I stuck it out. My final required me to debate another classmate. I was paired with a 40 something year old cop (I was 18 or 19) on the subject of “Should Marijuana be legal?” I think you can guess who won that debate, and it wasn’t me. This was before the internet and my opponent had easy access to all sorts of papers from his work to support his “no” position.
After years in healthcare, teaching and coaching, I became an expert at speech. But I just as easily could have given up right at the start. A speech loser. Starting any new skill, especially when you know you will be judged, is a rough time. When you go on a date and you give the “Default Response” because you aren’t high enough level to have unlocked any better responses, those early rejections can be especially painful.
This is why the early XP you earn on dates that will almost certainly end in rejection are so important. Each date and each rejection gets easier if you stick with it, and pretty soon those rejections start turning into “advance to the next stage”. Where you will probably get rejected, but at least you are now learning higher level skills and getting harder-to-earn XP.
People who date with the goal of finding “the best person possible” are really going to screw themselves here. The “best person possible” is probably 2 or 3 or 10 times your level. They are going to run circles around you. The best “training” for Speech is to find people around your level. You can make mistakes together and they are going to feel less punished. It’s just like in games where you start at “Easy” or “Normal” difficulty and work your way up. Don’t even think about hitting the “Nightmare” difficulty level button unless you’ve experienced and survived the worst that life can throw at you.
But… if you are ready for Nightmare dates, you might be surprised how much fun those can be while they last. Just come fully prepared.
Don’t worry about saying the “Right” or “Wrong” thing. Leveling up isn’t about content, it’s about context. When your confidence and experience is high, just relax and you will come up with good responses that the “lower level you” never could have had access to. Sometimes the “wrong” answer, delivered with enough confidence, can open up new options you could never have gotten any other way.
Practice, observe, learn, debrief. Don’t try to memorize a script. As you learn the process you will learn more about yourself and improve your ability to impress people with You.
Touch
Humans fly out of their mother’s womb knowing how to touch. It’s one of the few things you do fly out knowing. My mother was an OG Hippie from California. She raised me as a single mother doing pottery. We were always money poor but experience rich. Every weekend we would end up at a local Renaissance Fair or such where she would sell hand-made pottery to people who would appreciate it. I got to meet lots of people, hear Shakespeare, and even pet the occasional elephant.
When my school IQ-tested me then isolated me from the general population, because they didn’t know what else to do with me, that was a rough time. But I never felt that touch was “evil”, even when I had to endure … improper touching from adults. Changing to professions that required me to touch people pushed me to overcome any anxiety I had built up from cultural touch-phobia.
When you are good at touch, and people know it, they ask you to touch them. Just like with Speech, this involves a lot of practice. It also requires a very strong understanding of all aspects of Consent Culture so that everyone involved wants whatever is happening to happen. I’ve worked on thousands of women, mostly athletes and patients. When I was the trainer for the UCLA and USA Olympic Women’s track teams, I didn’t apply for those jobs. I was asked to fill the role by the lady athletes based on my reputation. I was only 22 years old.
Getting started with Touch skills can be tough, just like getting started with Speech. Perhaps enroll in a massage class, even if you don’t plan to be a professional touch therapist. Offer to practice on your friends or even first dates. People highly respect people who are good at touch, and who ask for consent before doing it. Touch is the ultimate icebreaker, even if it’s just a hug or a touch on the forearm.
That said, just like with Speech, confidence is held in high esteem. That’s why practice matters. Acting like you know what you are doing is going to open up more dialogue options that would otherwise be blocked. I happen to be really good at touching animals also, and animals appreciate me. That dog that barks at everyone else runs up to me to get rubs the moment they see/hear me. This works on humans too.
Touch is the gateway to intimacy. Intimacy and trust are the foundations of lasting relationships. Touch and sex are not the same thing. I will explain this in much more detail in the next paper. You might be shocked to learn how many people who think they are good at sex are crap at touch. And trying to engage in that sort of intimacy without touch skills is just… sad to watch.
Leveling Up Makes Everything Easier
Even if you are in a professional environment where touch might be inappropriate, the confidence you build from developing Speech and Touch skills translates directly to empowering your professional interactions. People can smell it if you are High Level and will show you due respect.
An example from soon after I landed in the Lesta studio in Saint Petersburg, Russia: A woman was dragging a heavy potted plant across the floor of the lobby. I could see 4 young men look at her briefly and then return to their conversation. I put my laptop down, and walked over to her. In my best sign language (because I didn’t speak good Russian) I asked her if I could help. Getting consent is important. She nodded and pointed to a far corner of the lobby. I picked up the plant and put it where she wanted it.
Then she cleared her throat, and in fairly good English she pronounced “Now there is a real man!” She wasn’t looking at me, she was looking at the four men that didn’t help her. And they weren’t looking at her, they were looking at me. They didn’t look happy. But every woman in that office was paying attention and my status at Lesta went up dramatically.
I only had to touch the plant, not a person, but the confidence I had from being higher Level made that interaction option available to me, when it wouldn’t have been available to a younger version of me.
Who is High Level?
If we imagine that there are 50 achievable levels in life, I would estimate that 50% of people are between L1 and L5. Another 25+% are between L6 and L10. Higher levels are weighted towards older people, not only because they’ve had more time to have experiences, but because they were alive (at least initially) in an era before we used machines to talk and think for us. Westerners are weighted closer to the bottom due to repressive cultural norms about touch. Corporate leaders who operate in an insulated manner tend to weight towards the bottom, while people who are in leadership positions that require a lot of social interaction (like real-space coaches and teachers) are weighted towards the top.
The point I’m trying to make here is that power in the West is not correlated with Level, and that’s why powerful people struggle so much with relationships. Self-awareness that you are low level (perhaps because you are young, or maybe all your dates go south for dumb reasons) is healthy. Please understand that the vast majority of people around you are also. So don’t be hard on yourself. Just be okay with the discomfort of learning, because this is a lifelong process. If you approach it like a game, then the XP itself becomes the goal, not the money, sex, love, children, security, etc. that you think you are looking for.
Level Asymmetry: The Most Important Thing I Can Teach You
I’ve always been desperate to learn as fast as possible, about everything. Even the bad things. In my relationships I mostly waited until I was 18 and then made a beeline for highly educated women twice my age. I started with my university professors. I kept doing that as long as it was practical. I hungered for their knowledge. This meant that there was (intentionally) a big asymmetry in Level in those relationships. I wanted to be with higher Level women. Early on they were fine with this as long as I was fine with being a boy toy. I learned this the hard way. I had to level up a bit before people took me seriously in regards to being relationship material.
But I stuck with it and it wasn’t long before I had very long term (longer than 10 years) relationships with women 15+ years older than me. I was literally trying to suck as much knowledge as possible out of every relationship. As I got older and ran out of people I could suck knowledge from, I switched polarity and started approaching relationships from a mentorship lens.
Having two people date or even cohabitate with a huge Level disparity isn’t necessarily a bad thing. It can be quite rewarding for both involved, and as anyone that has ever worked as a teacher can tell you, you learn a lot from teaching. You may have to navigate significant social stigma.
The hardest lesson I learned was that trying to Level up too fast can be uncomfortable to the point of pain. I learned this in both directions too. It can be overwhelming. You need time to process that much information. It can be tempting to just go all in when something is so exciting but both people need to understand that humans have limits. Both people should be sensitive to this and try to put pauses in there to avoid brain meltdown. Having a wipeout because you went too fast is traumatic for both people. If the information transfer is huge, savor that. You both have a good thing, no need to rush it. When you call for a Pause, communicate very clearly about why, so the other person does not interpret this as rejection.
Sooner or later, you will end up in such a situation. The challenge level is high, and the risks are significant. The rewards are also high for both of you. The stronger your Connection to someone, the more care you need to approach them with. If you attempt to enter the Soulmate State of Being, then this is absolutely critical to understand prior to Connecting to someone else on this level.
As I explain in my Soulmates paper, a Soulmate is not an object that falls from Heaven. It is a State of Being that you generate from inside you. This is why 99+% of people never find a Soulmate. Once you Connect to someone on that level, one hour becomes like ten. It can be too much. You have to take breaks, sometimes days or even weeks to pause and process the information exchange. This involves a lot of trust for both of you since being that Vulnerable is really scary.
In The Matrix, people can learn at almost infinite speed. Humans in 2026 can’t do that. We have organic limits which you may never experience. But they are there, and if you do push up against them you have to respect those limits.
So I Leveled Up. Now What?
Just having more choices in life because you’ve earned higher confidence with people doesn’t mean all those choices are good choices. I’m a firm believer in using the right tool for the right job. In the next paper I will teach you how to identify what the people around you want from you. Then you can use that information to decide if you want to give whatever that is to them, and how. You can also figure out when you should be declining requests from people, which is a core skill in dating.
When you go on a date, the purpose is to decide if you and that other people are compatible and might fulfil each other’s needs on some level. Are they moving in a direction that is synergistic with where you are heading? In most cases, you and the other person are not going to be compatible. Life isn’t that easy and people are diverse. That’s what makes humans so amazing. Learning how to rapidly identify that and gracefully get out is an essential survival skill for all genders. The other person is almost certainly going to misrepresent themselves to paint themselves in the best light possible. Thus in the next paper I give you tools to identify this and determine if you should disqualify them.