You have an ongoing, lighthearted chat with the bot (maybe it pings you now and then asking for updates.) Every once in a while it asks you more personal questions to switch things up and deepen its model of you.
Now and then it says "may I introduce so-and-so to the chat?" and introduces someone else who (on their side) has been primed to talk about the same topics and, at least according to the bot's internal models, is likely to hit it off with you.
Then the chatbot itself politely leaves the conversation but keeps listening and privately messages the both of you to keep things humming along, for example nudging one of you to ask for an in person date when the moment seems right (or helping you politely wind things down if you ask it to). After a date it asks you to spill the beans so it knows what went well and what didn't.
I think this could almost be made to work with the tech we have now; a fluent-but-shallow ChatGPT style chatbot is probably good enough for the task as long as it is augmented by some additional models to predict dating compatibility, recognize when things are going well or badly, suggest actions (like changing the subject to or away from personal topics, asking for a date, etc). And of course the models would improve over time as the system learns from its own successes and failures.
Whether this is dystopian or utopian is left as an exercise for the reader -- I'm married and 15 years out of the game!