Possible Clues:

• Cheerless
• Gloomy journalist returning to be dealt with immediately
• Rep designs tour that's fairly dismal
• Rep designs movement by being miserable
• Causing dejection
• The president interrupted, signed anyway, and that's heartbreaking
• Brooklyn dry cleaner's chore?
• Making miserable
• It might mean more relaxation but would mean less happiness
• Disheartening