I recently read Middlesex by Jeffrey Eugenides on T's recommendation. Some of it rang very true for me, some did not, but I am glad I read it and we have had some good discussions about it.

People who grew up reading a lot, in particular SF and fantasy, should read Jo Walton's Among Others. So many people I know, myself included, see parts of their own childhood and young-adulthood in it. I might recommend it to T. :-)