Read Gadamer’s Warheit und Methode (unless you have a pathological aversion to continental philosophy in any form). All understanding is hermeneutic and thus infinitely wheeling us around the hermeneutic circle. It’s the entry-point (without an exit) to answering Plato’s questions about questions. It’s how we learn and deepen language understanding. It’s how we interpret texts. It’s how science works, except that science enshrines its Methode as a sine qua non. It’s how we come to understand other people and why we can be continually surprised (or not!) by them.

The real shame is that academic fashion jerked violently in the direction of Derrida and company in the mid-to-late-60s before anyone had time to really dwell with and appreciate the power of Gadamer’s philosophical hermeneutics. His masterpiece was only published in 1960, when he himself was 60! It’s a mature and deep reflection on themes he had been studying for 40 years. Ricoeur grasped its power, of course, but the whole Habermasian-Derridan-Foucauldian critical project flavored Ricoeur’s approach. Richard Rorty gestured in similar directions, with less depth (and certainly far less phenomenological power).

But invest the time to read Gadamer. It’s worth it.