Potential answers for "Winked, maybe"

⭐⭐⭐⭐ FLIRTED
⭐⭐ TACIT
⭐⭐ TACITAPPROVAL
⭐⭐ IGNORED
⭐⭐ ONTO
⭐⭐ ALLKIDDINGASIDE
⭐ PLEADER
⭐ OLEO
⭐ AGE
⭐ MASSAGE

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Targets of a traveler's check?   Past its "sell by" date, perhaps   Billing accompaniment