Potential answers for "Start of an old advice column"

⭐⭐⭐⭐ DEARANN
⭐⭐⭐ MYOB
⭐⭐⭐ DOROTHYDIX
⭐⭐⭐ ASKA
⭐⭐⭐ ABBY
⭐⭐⭐ ASK

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Crude meas.    Place with multiple ports   Common street name