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ruefully

/ˈrufəli/
IPA guide

When you do something in a way that expresses regret, you’re doing it ruefully. If someone asks you about your Saturday night and you smile ruefully in response . . . well . . . you probably made some poor choices.

The origin of the word ruefully is a Germanic word that means “repentance.” But over time the word has adopted a slightly humorous tone, so you can go ahead and shake your head ruefully at your friend who has just put his boot on the wrong foot — you feel a little bit sorry for him at the moment. You might grin ruefully when asked about how many pairs of shoes you bought on your trip.

Definitions of ruefully
  1. adverb
    in a manner expressing pain or sorrow
    “`I made a big mistake,' he said ruefully
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