Example : My finances were in a deplorable state.
A lamentable decision.
Her clothes were in sad shape.
A sorry state of affairs.

Synonyms : distressing, lamentable, pitiful, sad, sorry

Example : Deplorable housing conditions in the inner city.
Woeful treatment of the accused.
Woeful errors of judgment.

Synonyms : execrable, miserable, woeful, wretched

Example : A criminal waste of talent.
A deplorable act of violence.
Adultery is as reprehensible for a husband as for a wife.

Synonyms : condemnable, criminal, reprehensible, vicious