This question asks about the positive or negative connotations of the word erstwhile.

Erstwhile means former by dictionary definition and as discussed and mentioned on this English Language & Usage site, and here and there on the wider internet. It's also considered archaic.

I'd like to know:

  • does (or did) erstwhile consistently carry any positive or negative connotation, or was it a clinically neutral term?

For example, does one remember an erstwhile friend more fondly than a former friend; or would one more readily embrace an erstwhile enemy than a former enemy?

What I've found so far: the ODO and MW dictionary and etymology entries are clinical, the ELU references similarly deal with denotation rather than connotation, the first web reference cited above deals with a connotation arising from an erroneous presupposition, and the second claims without proof that erstwhile references both beginning and end.

  • I've always considered it to just mean "former". That said, I think there is an unspoken slightly negative connotation to it, such that I'd probably rather go hang out with a former friend than an erstwhile one. That's probably a lot to do with words that are less-common in use seeming strange, and people tend to shy away from the unfamiliar as a rule. – John Clifford Mar 16 '16 at 9:10
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    Can you please clarify 'first web reference ... above'. / 'Erstwhile' always (ie about 10 times) seemed to invoke 'wistful' to me, so that's one connotation. It might be a rare one. – Edwin Ashworth Mar 16 '16 at 9:21
  • @EdwinAshworth It's the one linked to "here". I've now edited the links into the phrases for easy reference. – Lawrence Mar 16 '16 at 9:25
  • Thanks @JohnClifford. It's kind of weird how difficult it can be to pick up the connotations of unfamiliar words, even given online dictionaries and the internet. It lends support to learning by immersion and to the common advice to learners to read widely. Hats off to language learners everywhere. – Lawrence Mar 16 '16 at 9:26
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    @Lawrence isn't the 'wistful' association mainly because erstwhile is nearly always used in the sense of describing a defunct emotional relationship (friends, lovers, even enemies) and so the context generates a sense of something lost? – Charl E Mar 16 '16 at 9:39

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