book: What Do You Mean, You Can't Eat In My Home?
The book isn't universally bad (else I wouldn't have read to the end). The author makes some good points and has some good advice, but so much of it is wrapped up in a writing style that conveys "superior attitude" that I hope not too many readers follow her advice to give this book to the aforementioned less-observant relatives. If the book were only intended for the ba'al t'shuvah, the Jew who has become observant per Orthodox standards, maybe her approach would be fine -- though it would be short-sighted to assume that others wouldn't also read the book (like yours truly). But writing in that way while advocating that outsiders read the book is perhaps misguided.
The book covers the following topics (one chapter per): kashrut, Shabbat and holidays, modesty and women's issues, dating and marriage, life-cycle events, and education. Throughout the book, but particularly at the beginning, the author asserts that it's important to explain to people the truth of torah and centrality of mitzvot in your life (with a subtext, for your Jewish relatives, of how this should be true for them too). She gives advice about explaining these points that borders on evangelism (that is, she's suggesting that the reader evangelize his family), and she seems to think this is what the family members want to hear and/or that it will move them toward observance.
Ok, I'm not a ba'alat t'shuvah and maybe I just don't understand, but in my experience, as a convert and as someone who's had some extended conversations with ba'alei t'shuvah, that's not what families are interested in. They don't, for the most part, give a hoot about the intricacies of your theology; they do, however, care deeply about how this affects them and how they interact with you. They don't want a lecture on why kashrut is good; they want to know what has to happen so you'll eat in their home. They do not want to be rebuked if they turn on the guest-room TV while at your house on Shabbat; you can jump straight to "what you do is not my concern". They almost certainly don't want to hear how fulfilling you find it to wear a wig and pray behind a mechitzah, separate from the men, but they probably do want to know what will be expected of them if they join you for a Shabbat meal or come to services with you.
I think the book suffers from trying to do two things: give practical advice (the goal conveyed by the title), and sell Orthodoxy. No one reading this book will both need and benefit from the latter, so it would have been a much better book had it focused on the former. The best way to do that might have been to co-write the book with, or at least extensively interview, some of those family members. The author is writing from her own perspective, but especially when dealing with matters of interperonal relations, it's important to remember that one person does not see all involved positions clearly.
This might have helped fill out some of the personal anecdotes usefully. For instance, she tells a story of visiting a favorite aunt with her children and noting that the aunt had made a point of procuring kosher cookies -- which were dairy. They'd just eaten a meat lunch; what to do? Ok, that's hard -- but the part that caught my attention was when she said that after several visits, she finally figured out that eating a dairy lunch before going would solve the problem -- a solution that jumped out at me almost immediately. I almost never eat meat meals before going visiting (except on Shabbat); yes, this means I have to limit myself to interact with the world at large, but that's appropriate. That self-limitation wasn't part of the author's tool set from the start probably influenced the way much of the book unfolded.
I suspect that a convert -- any convert, whether the subject is religion, fitness, veganism, smoking-cesation, or new business practices -- should only dispense advice if he kept notes during his transition and refers to them during the writing. I think sometimes authors, who used to be on "the other side", forget what it's like over there, but they're new enough to the new lifestyle (as compared to being born into it) to not yet project sufficient self-confidence. If any of my friends ever see this kind of annoying behavior in me, I do hope you'll whap me with the clue-by-four.
I believe the author has the best of intentions and the loftiest of goals. She's trying to do a good thing here. I don't think she realizes how off-putting her style is to some of the very people she's trying to reach, and I think she loves her new life so much that she can't help extolling its virtues on the way to addressing the practical issues promised by the book title. This is why she would have benefitted from working with someone who doesn't already share all of her beliefs -- she needed someone who could say "that's very nice, but what does it have to do with inviting your folks over for Shabbat?".
So, bottom line: if you're a ba'al t'shuvah, go read Rabbi Adin Steinsaltz's Teshuvah instead. If you're the relative or friend of someone who's become more observant and you want to grok this, and just talking with your family member or friend isn't an option, read one of the dozens of intro-to-Judaism books (if your Jewish knowledge is weak) or look up specific topics (like kashrut) at reputable web sites. And if you find yourself holding What Do You Mean... in your hands, by all means go ahead and mine it for the practical advice if you like, but be prepared to skip most of the exposition.

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I think
The only books that newly-observant Jews and their non-observant relatives need are the collected works of Miss Manners, a.k.a. הרג״מם, which is short for הרבנית הגאונה מיס מאנערס, the פושקת הדור לעניני דרך ערץ.
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The book raised three potential arguments against education choices -- prestige, provincialism, and prosperity, with much of prosperity being bound up in "you'll be mooching off your parents to pay for this" and only a token nod to "but my grandchildren will be poor". I do not, of course, have first-hand experience, but I somehow doubt that that's where the emphasis really lies in most families. (What was the flavor of resistance that you got before the clue-stick took effect?)
The only books that newly-observant Jews and their non-observant relatives need are the collected works of Miss Manners,
Agreed!
(How did you get the Hebrew characters? One piece of hand-crafted unicode at a time, or is there a trick?)
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I suppose if someone was looking for financial contributions from nonobservant relatives to finance their own or their child's Jewish education, then it would be useful to have techniques for diplomatically convincing those relatives that their money would be well spent. Personally, if it came to that, I would rather forego the money.
(To their credit, my mother and her partner, despite being devout agnostics, helped me out during my stay in yeshiva, without me giving them any more reason than "the student loan hasn't come through yet and my out-of-pocket expenses are higher than I had anticipated". We most recently thanked them for their generosity at our younger son's bris, when he was named after my mother's partner.)
How did you get the Hebrew characters?
GNOME has a "Character Map" desk accessory. There are other techniques, but that's what I used in this case.
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I've never known you to need a clue-by-four, Monica, but I stand at the ready, should it ever be neccessary. ;)