Your Personal Guide to Authentic Wanting

Knowing how to want in dating is difficult and personal. My subscribers deserve some personalized guidance.

The most common obstacle to people’s dating is that they don’t know how to want, dating-wise. They say they want a happy relationship with a great partner. But when you press for details, they have none. Ask most people what makes a great partner for them and you’ll often get:

• a cliché — hot and funny

• a symbol — tall and went to an Ivy

• a vagueness — good vibes

• a triviality — likes my favorite movie

• a vague symbolic cliché triviality entirely unrelated to the lived experience of being in a romantic relationship with someone, aka the post-2016-OkCupid special:

Dating like this is driving around without a map or a destination. Taking street turns based on vibes can occasionally get you somewhere marginally more interesting than the point you started from, like a Chuck E. Cheese. The Chuck E. Cheeses of aimless dating are situationships burning through a short fuse of horniness / boredom / fear of dying alone. “Maybe the next one is the real deal.” Would you know a real deal if it hit you in the face? What would make it different? “She’d be hotter and funnier and will want to rewatch 21 Jump Street.” Ok then.

If someone’s too ugly for Chuck E. Cheese, they make the opposite mistake: “I’ll keep lowering my standards until someone bites.” So your relationship vision is someone who’s not a catch and knows it? That’s going to be your opening line? If you’re not broadly attractive you have to narrow your market, not widen it. You need to be laser-focused on what you want and what they want from you. Put all the weight on idiosyncratic compatibility so that broad appeal doesn’t matter as much.

But when people don’t know how to have their own specific desires, they forget that other people have them. They chase general dateability, and get insecure over the impossibility of being the hottest, funniest, best-vibey person on the mass market.

I’ll have a whole chapter on the difficulty of expressing and acting on authentic desire. It’s a complex issue of epistemology, social dynamics, and psychological resistance. But today I’m just going to solve it for you.

Ask Yourself

Though I don’t advertise it, a good number of people have reached out to me through the years for dating consulting. Some want an ongoing coaching engagement, others just want a rewrite of their app profile. In each case, the first thing I do is ask a bunch of questions about what they’re actually looking for, and who might be out there looking for them. I try to get clients to seriously introspect and get past the OkCupid-level bullshit. To focus their selection and dating strategy on the things that actually matter to them in a relationship. Whatever else we end up doing, people find this exercise valuable.

I want to find out if this can be done in writing and at scale.

Below the paywall is a link to a six-point questionnaire about desires and matching. These questions are open-ended, and you should plan to spend at least 5-10 minutes thinking each one through. It can be completely anonymous if you want. After you fill it out, the following things will happen for you:

1. You will gain awareness and clarity about what you’re looking for, how to go find it, and what your personal dating market looks like based on what you want to give and to receive.

2. If you want, we’ll schedule a follow-up session where I would ask you more questions over text.

3. If you want, I’ll write you a brief personal assessment of your wants, selection challenges, and dating market. Your own special handcrafted personality quiz that’s actually useful.

And here’s what I’m going to do with it:

1. I will read your answers carefully and learn a lot from them about people want and how they see themselves. Maybe even write wiser posts as a result, idk.

2. I will scrub all identifying information from them (if you chose to provide any), like ages, company names, cities, etc.

3. I will send the clean transcripts to my AI-developer friend who will train an LLM to do the follow-up and assessment in my style.

4. If the LLM does a good enough job by my standards, I’ll offer it as a free option for people who want to do the exercise and get the assessment without my personal involvement.

5. If the LLM sucks, I’ll still be happy that I got to reward my paid subscribers with some personal attention and hopefully help them out.

And if the free LLM version becomes popular enough, I’ll have a database of people’s true relationship desires that I could use for matchmaking. I would set the responders up in perfectly tailored relationships and solve the loneliness crisis forever. It’s a big “if” to be sure, but it’s certainly worth trying.