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I am a second year pure math major at university. I took a class on social theory last semester, and did not enjoy it very much because the texts seemed lean toward obscurantism to the point of meaninglessness (eg. Hegel). In mathematics, one knows that if one is confused, it is because the material is difficult, not because it is meaningless (because the meaning of terms is clearly and unambiguously defined a priori). In social theory, I sometimes felt like it was hard to tell if I was confused because the material was conceptually difficult, or just verbiage that could be generated by GPT-3 and hailed as "profound" by academics in the field.

Rant aside, I have really enjoyed the little exposure to analytic philosophy (Frege, Russell, etc) I have had, and wanted a more serious introduction for someone with a technical background. A comprehensive introduction that is not dry (ie. motivated by reasonable philosophical questions an ordinary person might have) would be appreciated. Where should one start?

Thank you!

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I recommend you to begin with Gottlob Frege's Collected Papers on Mathematics, Logic, and Philosophy. Here is the publisher's description on which I wholly agree (I add the contents below):

A magnificent collection of work by the father of analytical philosophy

Gottlob Frege is widely considered one of the most influential minds in the history of philosophy, having spent a lifetime delving into the nuances of language and mathematics. Widely published on logic, analysis, geometry, and arithmetic, which he regarded as the purest form of thought, Frege's analytic approach to philosophy set the stage for the field's eventual linguistic turn. Collected Paper on Mathematics, Logic, and Philosophy is a compilation of his collected works across fields, allowing readers to share in his evolution of thought and catch a glimpse of a legendary mind at work.

Frege has a lucid style, directly addressing to a well-articulated subject of discussion. His approach is befitting philosophically inclined mathematicians -not unexpected for one who was a mathematician by profession. These features should not give the impression that his writings are philosophically parochial -Michael Dummett's books and articles on Frege attest the opposite.

Besides, a usually missed point, Frege was quite knowledgeable about and conversing with the philosophical works of German circles, which many philosophers that profess the analytic tradition prefer to keep at a distance.

So, why not a textbook-style book? If you can devote enough time to read, that is all right, too. Then, I recommend you to pick out books from the series Routledge Contemporary Introductions to Philosophy.

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