I'm looking for engaging non-fiction or social theory books about American Culture.....

I’m specifically interested in contemporary critiques of individualist vs. collectivist societies, the challenges of meaning-making in the western world, critiques of American “exceptionalism” or theories on individual’s notions of self and role in society…
Very broad I know, but really just looking for good, thought-provoking reads that are not overly academic.

Sounds like you’re looking for something along the lines of Toqueville’s Democracy in America, only more recent?

Exactly!

Bowling Alone?

Go find “The Geography of Thought: How Asians and Westerners Think Differently…and Why” by Richard E. Nisbett. Very good read.

The Rise and Fall of the American Teenager
The Way We Never Were