Potential answers for "One who knows if you're out?"

⭐⭐⭐⭐ UMP
⭐⭐⭐ ATTY
⭐⭐⭐ CPA
⭐⭐⭐ MAESTRO
⭐⭐⭐ SPORTSCASTER
⭐⭐⭐ CBER
⭐⭐⭐ OLDPRO
⭐⭐⭐ OLDHAND
⭐⭐⭐ ORACLE
⭐⭐⭐ STENO

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Dates regularly   Distressed   Subjects of conversation