In a sentence: Bid/donate/pay what you want upfront, held in escrow upon a successful outcome confirmed by all involved individuals. At payment time, you can change your bid/donation/payment based on your more-fully-informed evaluation of the dating app’s value.

I don’t have the time or particular interest, so someone else should go build it and see how it goes.

The current generation of dating apps emerged during the peak of B2B SaaS. So, unsurprisingly, they monetize in the same familiar way: gating features (visibility, in particular) behind tiered monthly subscriptions, with heavy discounts for longer commitments. B2B SaaS only understands retention, engagement, and recurring revenue. But the key marker that a dating app has “worked” is when you churns. The business thrives only when people keep dating forever, but no one wants to do that. The business also wins when you dejectedly return. No one wants that either. Everyone on a dating app wants to exit permanently, as soon as possible.

What is this model exactly?:

• During the onboarding flow, you place an unrestricted bid, answering the question, “what is [successful outcome X] worth to you?” During the offboarding flow, when you feel that [successful outcome X] has happened, you can revisit the bid you placed. As you leave, you pay for the value the app gave to you. Grasping at this number is an arational pursuit. You have no good way of actually determining this worth relative to you-right-now, but you still have to give it a shot.
• The app only receives money when everyone involved agrees and confirms that the app did its job. Monetizing in this way aligns its incentives with ours. The app profits if and only if we found it was valuable. It bears the risk of actually creating high-quality matches.

What is [successful outcome X]? The “billable event” should be at the boundary where the app starts to overstay its welcome. So my guess is a “talking stage”. Anything more “serious” is too far removed from the work the app does, and would be hard to verify. GPT-4o recommends the billable event hinges on the following questions. The business would only make money when everyone involved answers yes to all three:

• Did you meet this person in real life?
• Would you like to see them again?
• Would you like to pause your profile to explore this connection?

By design, this model captures full willingness to pay. But only if you can trust that people report their valuations honestly. This is a core problem that this model suffers. You can’t really assume honesty when freeriding is so easy. You can “lie” about your valuation, you can delete the app instead of paying, you can simply forget about it as your life goes on.

For some (for most), the answer will be $0. But it’s not all that expensive to run lichess, the only viable scaled free online chess platform, and only 0.3% of users donate. This pricing model is a bet that the app will create enough high quality matches that enough people will feel enough gratitude that they’ll pay enough money to keep the servers running. It’s possible in principle!

Another core problem is: how much am I willing to pay? What is the present value of a transformative partnership?

Really, how do you actually estimate the present value of a transformative partnership? There are good reasons to think that this is impossible.

Why? Henrik Karlsson explains it well so I’ll let him do it:

• The type of person I’m assuming we’re looking for here is 1) someone that you will find fascinating to talk to after you’ve talked for 20,000 hours, 2) you feel comfortable with them talking through the hardest and most painful decisions you will face in your life, and 3) the conversation is wildly generative for both of you, in that it brings you out, helps you become.
• That open conversational space, which is the heart of our relationship, is not something I can explain; it is not something I knew I was looking for; I’m not even the same person after having been there. It does not look anything like I imagined a relationship would or should look
• What Doestoevsky is doing to his characters…is loving them. That is: he is crafting a space where the unknowable engine at the bottom of their souls starts generating words that reveal them to themselves. He’s bringing them into being by attending to them with open curiosity.
  
  “If I give this person the loving space where they can express their word for hundreds and then thousands of hours, what will happen then? What will they transform into?”
  
  This, I think, is a healthy way to think about love. It is about being invested in someone’s continual expansion

Loving partnership irreversibly, unpredictably transforms you. You do not know who you will become, nor how, nor when. You-in-the-future will have different values, beliefs, preferences, than you-right-now. They will not see the same world as you-right-now do. So you have no idea how you-in-the-future will view the way things went. So it’s hard for you-right-now to know how much you should pay. You’ll grasp at it and give a wild guess, at best.

There is yet another layer. What you pay the app for isn’t the loving transformative partnership itself, only the possibility.