Potential answers for ""Do I ___?" ("Should I?")"

⭐⭐⭐⭐ DARE
⭐⭐ ISAS
⭐⭐ EVER
⭐⭐ AULD
⭐⭐ NOT
⭐⭐ ERE
⭐⭐ POEM
⭐⭐ EEN
⭐⭐ ASIT
⭐⭐ SEEN

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"So long, friend!"   Org. concerned with free speech   Italian city where pesto originated