It takes a talented writer to bring out the humor in a serious topic, even more so when it's something that happened to the writer him (or her) self. I think society has made a lot of progress towards understanding and accepting homosexuality. But transgender is a whole other thing. It strains the tolerance of otherwise accepting people, who just don't get it. Their issues get lumped in with gay and lesbian issues, but it's a whole different thing.
Jennifer Finney Boylan's She's Not There is something I encourage everyone to pick up, then. Not just because it'll help towards understanding, but because it's a good and funny and heartbreaking read as well.
Boylan's best friend is a favorite writer of mine, Richard Russo. They taught together at Colby College and remained friends all their adult lives, even as the guy Russo knew as Jim got to the point where he could no longer deny what was inside of him and began going through the process of becoming a woman. Despite the presence of a crossdressing villain named Finney in Russo's novel about academic life, Straight Man, I wondered if Boylan was more the model for Hank, the protagonist pain-in-the-ass prankster. One of my favorite moments in She's Not There was a reproduced email correspondence between the two when Boylan was in transition. Russo poured his heart out about his difficulties in trying to readjust to the fact that his best drinking buddy was now female and closed it with something like "Then again, my biggest problem has always been myself." Boylan shot back with a one-line reply: "Funny, my biggest problem has also always been yourself."
One great thing about Boylan's two memoirs that I've read so far is that they read like novels: great characters, a plot that really moves, lots of detail. I like how, in this one, Boylan takes advantage of her unique perspective. Anyone who's ever wondered whether women get discriminated against in buying cars, who has an easier time shopping for clothing, if men and women actually think differently, etc. can actually find some answers in this book from someone who's in a position to tell you. It's a wonderful book, I highly reccomend it.