- causing sorrow or pity; lamentable
- feeling or showing sorrow or pity; mournful
- feeling or showing regret, esp. in an abashed way
When you lose your chance at a big promotion because of an error in judgement, your facial expression might be an example of a rueful expression.
(comparative more rueful, superlative most rueful)
rue + -ful
- He made it and gave her a rueful smile before dropping down beside her.