I was just lamenting this morning how my todo list, a set of tasks for the next few days, was depressing me. When I wrote it, it was a great joy to get all these things out of my head, but now that all I had to do was follow them, it felt mechanical and boring. I could rewrite the list and gain some excitement about a few of the tasks that way, but instead I've been trying to figure out the why of this feeling, and your post gets me right back into it.

I think there's an ideal working state -- perhaps the state of Flow is describing it, or perhaps that's simply some peoples' ideal working state, and there's a more general form of it (I'll use flow for this comment). In this ideal working state, we're constantly encountering problems that are within a known scope. So they're problems -- we don't immediately know how to handle them -- but they're scoped problems, so we know how to figure it out. This is fun, because there are problems, but they're solvable problems.

Dating advice you describe as useful does the opposite of flow -- it creates tasks. Tasks, because they don't require the overcoming of scoped problems, are boring. Taskifying things make them routine, easy, and boring. Taskifying itself can be in flow. Re-taskifying recreates the sense of flow and allows a task to fall within that flow.

What I would want isn't taskified advice, it's the experience that would allow dating to feel flowful.

(I've italicised to try to mark flow as a technical term. Please let me know if I should change the format.)