If your elaborate magic trick goes awry, and instead of pulling a rabbit out of an audience member's shoe, you set the shoe on fire, you might give a rueful smile. Rueful means apologetic or remorseful.

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."

Definitions of rueful
  1. adjective
    feeling or expressing pain or sorrow for sins or offenses
    synonyms: contrite, remorseful, ruthful
    penitent, repentant
    feeling or expressing remorse for misdeeds
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