Question on use of discretionary hyphens

Hello,
I hope someone can solve the following conundrum!
I want to make sure that compound words (ex: official-looking) do not break at any syllable at the end of the line. It then looks unsightly when the word has two hyphens.
If I put a discretionary hyphen at the beginning of the second word, then neither word will break and it will break at the hard hyphen. This works but I do not understand why. Further, if I put the d. hyphen in front of the first word, then neither word breaks nor will it break at the hard hyphen, which is not a good result.
But then the problem deepens.
I also do not want the words prior and after an em dash to break. Breaking the words in this instance also looks bad. Again, if I put the d. hyphen before the second word, the phrase will break at the em dash but neither word will break except under the following condition:
If the second word has only one syllable the first word will break.
I could fix that by puttinga d. hyphen before the first word, but then it will never break at the em dash.
Any ideas?
Thanks,
Tom

Sorry, I probably can't actually answer your question, I'm just trying to save you from the dustbin of page two.  I tried to write up a GREP style suggestion for you, but maybe you've already considered this? I decided it'd probably take two GREP searches to apply No Break to either side of a compound word separated by a hyphen, and it felt like an awkward suggestion. Then, I tossed the question at Google, and found that Kenneth had posted about this issue in 2007. Interestingly, that thread covers this question (and a partial answer, why a GREP style won't work), and the odd behavior of the discretionary hyphen when used in a compound word with No Break applied.
Maybe there's some sort of obvious non-GREP answer. I often manage to gin up hacky solutions in these kinds of cases with a zero-width space, e.g. [word][nonbreaking hyphen][ZWS][word], in a paragraph style with hyphenation turned off. However, I doubt that's the answer, and if there is a good non-GREP answer, I simply can't consume enough coffee to make my brian generate the answer. Best of luck.

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