When I saw this book at the library, I thought it would probably be kind of dorky, yet I couldn't resist checking it out because it seemed like there was a slight chance it might somehow be interesting or inspiring or moving in the way the "It Gets Better" campaign has been. Unfortunately, my first instinct was the correct one. Many of the letters offer exactly what you would expect--assurances that the 16-year-old self is smarter/cuter/more talented/better loved than he/she thinks and advice about valuing their parents, working hard for their dreams, not being afraid to fail, etc. While most of the pieces are just rather mundane, some of the writers are so full of their own achievements that it is nauseating (Suze Orman is the worst of these). A few of the writers basically blow the task off (Alan Rickman writes "If, in future years, anyone asks you to give advice to your sixteen year old self, don't.") A few are skilled enough or take a fresh enough approach to make their page or two interesting (Alan Cummings, Moon Zappa, and Sandra Bernhard are three of this)--but there just aren't enough of those.
At the end of the book, the editor leaves a number of blank pages for readers to write their own letters, which can be posted at http://dearme.org. I thought about trying the exercise, but decided I wouldn't have anything more meaningful to say than most of the writers represented in the book, nor could I speak as movingly to teenagers as many of the folks in the "It Gets Better" campaign. It would seem more useful to me to write a letter to my 80-year-old self to remind me of the aspects of myself that I want to hold onto as I enter old age--but, of course, that's the perspective of someone getting up there!
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