I don't understand the meaning of に in this sentence:
Is 切り出すに切り出せず fashioned after some particular grammar? I can't really think of an interpretation that sounds natural.
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「Verb + に（or にも） + Same Verb in potential form + ず」
is a very common phrase pattern that expresses one's inability or hesitation to perform the action described by the verb.
"I have not been quite able to bring up (this) topic until today."
This is more of a grammatical construction where you have a verb in base form plus に followed by a negative potential form of the same verb. It basically means that for some prohibiting reason, you couldn't do ~~~ even if you wanted to.
終電を逃したから、帰るには帰れない。(Paraphrasing, "I missed the last train and I have no way to get home.")
It looks like in the sentence you shared, it would mean something like, "(No matter how much I wanted to) I had no way to bring it up..."
Semantically, it means 切り出したかったのに切り出せず. (切り出す = to broach (a topic))
[dictionary form of a verb] + に + [nai-form] + ない is an uncommon, emphatic, and literary set phrase which means "want to ～ but can't", "too bad/extraordinary to ～", etc.
- 泣くに泣けない状況 a situation too bad to cry
- 笑うに笑えない話 a story too extraordinary to laugh at
- この料理は食うに食えない this dish is too bad to eat (tastes awful)
- 食うに食えない生活を送る have difficulty to live on (because of poverty)
I think this に corresponds to either of the two definitions of this page: