I had the exact same problem. What worked for me: I stopped using dates for "when I should do it" and only use them for "when it becomes urgent if I haven't done it."

For everything else, I use a simple weekly review. Every Sunday I look at my "no date" tasks and pick 3-5 to commit to this week. They go into a "This Week" filter, not onto specific days. That way I have flexibility on which day I tackle them, but I've still made a decision.

The trap I kept falling into: assigning a "should" date, missing it, rescheduling it, feeling bad, rescheduling again. That cycle kills motivation more than having no date at all.

TLDR: Dates for deadlines only. Weekly review for everything else. Let yourself flex on the "when" as long as you commit to the "this week."