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I generally work from the Oxford American College Dictionary, because that's what Google pulls from if you search "define x" and I'm getting hung up on the definitions of rue compared to rueful.

Rue is defined as "to bitterly regret and wish it undone," and rueful has the same definition, but the OACD adds "especially in a wry or humorous way."

https://en.oxforddictionaries.com/definition/rue https://en.oxforddictionaries.com/definition/rueful

Merriam-webster defines rue as "regret or sorrow" but defines rueful as "exciting pity."

https://www.merriam-webster.com/dictionary/rue https://www.merriam-webster.com/dictionary/rueful

Would it reason that "rueful" adds a connotation of wry humor versus "rue?"

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    I don't think the ODO definitions you mention for 'rue' and 'rueful' match as well as you imply. rueful: 'Expressing sorrow or regret, especially in a wry or humorous way. ‘she gave a rueful grin’' ' I don't see how one can express bitter regret in a wry or humorous way. – Edwin Ashworth Feb 9 '18 at 23:50
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All other online dictionaries do not mention the wry humorous aspect of rueful . Only vocabulary.com notes that:

The adjective rueful sincerely expresses regret, but it manages to do it with a hint of humor. Rueful shows up a lot in descriptions of remorseful grins or apologetic smiles. If you're sorry about something you've done but you can still laugh at yourself a little bit, you feel rueful. The word itself comes from the verb to rue, which means "to regret."

  • This is an excellent and succinct find, thank you for the clarification! – Christopher Issac Feb 9 '18 at 21:48
  • @ChristopherIssac - Don't forget to mark this Answer as the Accepted answer if you feel it answers your question :) – Brian Lacy Feb 10 '18 at 0:05
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    That's an excellent description. It's a sort of inherited baggage of the word (the inherent meaning of the word hasn't changed - it means regretful, sorry, chastened - but it's so often used in combination with grin or wry grin that's it is a cliché). – Will Crawford Feb 10 '18 at 0:16

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