That's pretty much Rocket Money
But in spirit, you would probably only describe it as truly "working" (in the sense of accomplishing its claimed purpose) if as soon as it ran out of things to suggest cancelling, it suggested cancelling itself. Which it doesn't. So no.
Same as a dating site/app — a dating system truly designed in spirit to accomplish its claimed purpose, would seek to minimize the time anyone spends using the app before uninstalling it. And no such site/app exists. (Although it could — as this is basically the business model of a professional matchmaker, where you pay a large lump sum up-front and then they're beholden to do unbounded work to find you a happy relationship. So they seek to minimize how much of their time you spend, by finding you that happy relationship ASAP.)
It would be an interesting world if we outlawed auto-renewal for services that you need to actively use in order to get any value from them. When you're paying for Netflix, you aren't paying to watch movies, you're paying for /access/ to movies you can watch. The flip side is that the maximum potential service quality would decrease if revenue decreases -- which is also why ad-supported services prevail. If all players are subject to the same rules, that would either end up as a decrease in licensing costs or a focus on quality content over quantity. If they aren't producing exclusive content, they are beholden to the quality of the market. Either way, that should encourage quality content to be made over saturating the market with content.
Unfortunately, pipe dreams will remain pipe dreams.
Having legislators outlaw bad business practices is in general very slow; if competition works then it seems there should be a niche for a lump-sum/fixed commission-based dating service where they match you with the people in their database most likely to actually be compatible with you. But now that creates a new problem of measuring "successful" outcomes in matchmaking, which will be near-impossible to measure and easy for all parties to game, if it's mostly transacted by app. But it sounds in principle like the business model for traditional introduction-based matchmaking (the matchmaker only gets a good reputation if they have some successes, and most prospective customers will only be willing to pay $ for say 3-12 months).
EDIT: makes me wonder: eHarmony never opened matchmaking offices.