What I Learned From My Date-Me Experiment

Last year, I published a “date me” survey with ~60 questions in an attempt to find a serious long-term partner. I designed it with a few categories – lifestyle choice compatibility (stuff like age/location/relationship style/future plans), sexual compatibility, value/personality alignment, and questions that would filter me out if they valued stuff I didn’t have.

Unbeknownst to the respondents, the survey was scored, with various questions weighted by how much importance they had to me. The result was a big spreadsheet of a few thousand people sorted by their survey score. I contacted the top three scorers; of those, two responded, and logistics allowed me to meet up with one of those two.

This scorer was Nate Soares, someone I’d met before; he’s a deep-rationalist who’d shown up to a party or two (including my naked mask party, wearing an anglerfish mask, where he didn’t speak a word the entire time, and nobody could figure out who he was for months afterwards. This was hilarious). I hadn’t particularly found him memorable; he was nice, but I hadn’t felt attracted to him.

He proposed our first date be a yolo 3-day airbnb in the woods. I like yolo spirit and accepted. It was awkward and terrifying; I didn’t feel attracted to him, but had sex the first night anyway in the spirit of figuring out if we were compatible. Things felt stilted (to clarify, the sex did not feel stilted), like we were coming from two different countries, but on the third night one of our conversations felt a bit of a breakthrough in connection, and we decided to attempt actually dating.

Our second date was a week long (estimated 50% chance of working out), our third date a few weeks long (estimated 10-15% chance of working out), and our fourth date was moving in together for a three month trial period. We tried an explicit, high-pressure escalation to speed up “figuring out if we want to be life partners”; as each successive date seemed to hold promise, we figured we should turn the knob up even further to see if anything exploded.

We’re currently 2.5/3 months into the living together part, and it’s probably not going to work out; we estimate a 5-10% that we’d want a ‘serious long term partner’ role from each other. The problem mostly (but not entirely) resides in communication difficulty; we speak two very different languages, and often very basic conversations get sidelined by hours of processing (mostly my) emotional fallout from miscommunications.

(He’s still a really wonderful person in a myriad of rare and valuable ways, and many people with a more compatible language with him would probably have a fantastic time dating him. I wrote up a ‘Why You Should Date Nate‘ here, if you’re a lady and interested).


This experience was super useful for me, and clarified a few things.

First – the organic selection process (where you meet up and vibe first before pounding your way into Serious Relationship territory) probably does good selection for communication styles. We subverted this and ended up with a lot of communication difficulty, which is an incompatibility that we probably would have picked up on and stopped things a lot sooner if we’d tried to go the organic route.

Second, it made me really aware of how flexible attraction can be. I wasn’t into this guy at all, but with some sustained effort and a few days of close proximity I felt my first stomach butterflies (and I’m now extremely attracted to him). This is crazy to me, and opened up a whole new world – how many other people who aren’t attractive to me, could become attractive to me with some effort? This does seem to hold with how other people select their partners, too; proximity has historically been one of the greatest predictors of dating – people you go to church or work or school with. And people falling in love in arranged marriages seems like it might be more the norm than the exception.

The same holds true for non-romantic social groups. I have a specific social group I’ve had a strong hand in crafting; it’s full of a lot of people I knew I liked already, and a few people invited by others who I wasn’t initially excited about. But over time they really grew on me, and at this point I would likely invite them myself due to this developed fondness. And it’s strange to watch “how much I like someone” be so moldable! Now, instead of “I don’t find you particularly interesting (my term for this is tofu-human),” I view most people as just… in various stages of pre-liking, where the only thing preventing them being fascinating to me is just a lot of proximity.

It’s like inside me I have a little garden of affection, where I feel affection for anyone who steps into that garden. I will be loyal to them, help them if they need it, devote time and attention to them. This garden is (mostly) unconditional; it does not decide who within it gets its fruits, or if they’re worthy enough to eat; the only requirement is to be in the garden.

But my garden has the gatekeeper, who decides who to let into the garden. I might see someone who doesn’t have their shit together, who needs a lot of emotional labor, who might cause me a lot of pain, who I will struggle to understand, and know that I could love and care for them. The question is not if I have a garden that would accept them, but rather if I want to let them into my garden. My gatekeeper is cold and brutal. It checks how many resources my garden has, how many people are in there already, how sustainable it is. It evaluates potential entries on concrete facts – how emotionally mature are they, how intelligent? How much power do they have? Do they have money? Are they socially strategic to be associated with? Will they increase your garden capacity to hold others in the future?

And so, right now my choices around who new to allow into my garden is associated mainly with an unflattering calculating strategy. My life is a chess game, and these players are the potential pieces. This is particularly true with my romantic life right now; I’m looking at potential mates as strategic moves. Really I suspect this is what I was doing all along, and likely what many other people are doing, it was just much more subconscious before.

But the gatekeeper itself is not allowed in the garden; once in the garden, the newcomers are free from evaluation. If they drop in power, if they stop helping me, if they start absorbing way more emotional energy, then in my garden they remain; doused in affection and unconditionally accepted. My garden carries many powerless people from earlier places in my life, or from high-proximity adventures, or people who came in attached to someone else who my gatekeeper wanted more. I am not evaluating them, my love for them is not dependent on what they can offer me; they simply reside in my heart. I have no regrets about this and it’s not an issue for me that my gatekeeper might continue to reject people similar to them.

(also to be clear, the garden analogy isn’t perfect and I’m oversimplifying; people don’t always stay in my garden forever, it’s not exactly binary if you’re in/out of the garden, there’s different garden levels, and i don’t think literally everybody would be automatically and unconditionally drowned in affection once they got past the gatekeeper)

Thirdly, my dating experiment gave me the cool sensation of dedicating loyalty to a romantic partner.

As in; once I dated someone where the relationship wasn’t great. He did things that really upset me, and I put in a lot of effort to managing my own emotions and trying to get the conflicts to stop. Later, I dated a new person, and was shocked at how comparatively easy it was. I realized I shouldn’t have been trying so hard in the past relationship; I should have noticed the strain and noped out of there, that it was a sign that we were incompatible.

But also people in long term, successful relationships often talk about commitment – sticking with it when the going gets tough. You can’t just nope out if you don’t like it, you have to work hard and build the relationship like a shared project. If you flake out, you’ll never have a long-term relationship at all! No relationship is perfect, you have to try. This is what commitment means.

(Or is this just a cope? I know someone in a 30-year abusive marriage who says exactly this.)

So which is it? If you’re in a relationship and it’s really hard, are you in the reality where you’ll nope out and go wow thank god I didn’t stay in that awful relationship”? Or are you in the reality where you nope out when it’s tough and go “wow why can’t I ever find a long term partner”?

When things get hard, a part of me is always running that question, and evaluating a conflict for “should I break up because of this”. I’m never just having a conflict, I’m also trying to decide if this conflict is worth the relationship. But with the time boxed setup of this relationship, where we “committed” for a certain length of time, I found that I was able to just have conflicts. I dedicated myself to making the relationship work no matter what, for three months. This allowed me to give the conflicts my all, to try way harder than I would have otherwise, to remain undistracted by the evaluation process of ‘does the intensity of this conflict mean this relationship isn’t worth it’. And this was awesome. I learned a lot about myself, and grew much more optimistic about being able to make a very serious relationship work long-term in the future.

Or in a way, I was able to let him into my affection garden (or the version of it that is for romantic partners or something) for a time-boxed period of time, and get to actually explore the relationship from after the gatekeeper, instead of running my gatekeeper on what was happening.


As it stands, after Nate moves out we’ll probably keep dating more casually, but while each making more deliberate attempts to find more compatible serious partners (we are both poly, anyway). The whole process has been super bittersweet. It hurts to be so close to someone you care about so much, and to see so close potential for a flourishing partnered life, and have it just not quite fit. It’s really tragic, but I don’t regret any of it.

I’m still running the date-me survey, and might continue keeping an eye on results from there, but I don’t think this is a full substitute for in-person hunting. My plan is to attempt to orient my social life such that the kind of person I organically meet also is more likely to have the kind of values and resources my gatekeeper desires.

4 thoughts on “What I Learned From My Date-Me Experiment

  1. Sticking when the going gets tough–My relationship with my partner is the easiest I’ve experienced. We communicate and negotiate well and are still heads over heels crazy in love with each other four decades on. Sticking for me was never because of my partner when times got tough. If there were problem spots it was because of problems within our environment, generally issues I had no control over.

    YOLO–Years ago a supplier was talking where I was working about how he and his wife planned on traveling when they retired. She died before that time and his message was that one shouldn’t put off doing what’s important. Thirty years ago we quit our jobs, moved to the state we currently live in where we’d purchased densely forested acreage. We’d started three buildings but they were just shells when we moved to our home. The first decade wasn’t easy but it wasn’t hard either. Our environment nourished us in ways we hadn’t experienced in our prior lives and we were able to make a living working at home. For me that was mostly outdoors in a building with doors and windows open, even when temperatures dropped well below freezing. I love the visually and aurally complex environment I live in. The other aspect to how we live is that the way we live forces us to work together on projects big and small. These projects have deepened our bonds to each other and enriched our relationship’s history.

  2. I wonder how much the communication problems were simply brought to light by the ultra-fast ramp up, vs whether the quickness might have caused them? I’m contemplating a theory whereby two people who date and slowly increase the intimacy and stakes in a relationship have more time for their communication strategies to converge to a more compatible middle ground?

  3. Now I’m seriously wondering if anyone tried to game the survey by picking the answers they thought you wanted to hear instead of the truth.

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