[adamstober]

Thanks for the feedback. Agree that there needs to be some exploration to making it work, and I think the idea of asking for contingent pledges is an interesting one! In one form or another, I don't see why free online services (dating or otherwise) don't periodically and methodically prompt users for contributions a little more often.

Wikipedia outright asks for donations, and certain mobile apps already ask highly engaged users to rate the app. Extending that to the next level would simply shift the prompt from "Donate to our non-profit" (Wikipedia) or "Rate this app?" (free iOS or Android app) to "Support our (free, for-profit) service with $?"