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- All happy families are alike; each unhappy family is unhappy in its own way ( the opening line of Anna Karenina )
- As miserable as sin
- Happy sad ( a bitterweet feeling combining both happiness and sadness )
- How sad is that?
- It is not a lack of love, but a lack of friendship that makes unhappy marriages ( Friedrich Nietzsche quotation )
- Miserable specimen
- Sad sack
- Sad state of affairs