Potential answers for "Didn't play it safe"

⭐⭐⭐⭐ DARED
⭐⭐⭐⭐ RANARISK
⭐⭐ DARE
⭐⭐ DHED
⭐⭐ SAT
⭐⭐ SATOUT
⭐⭐ PUSHTHEENVELOPE
⭐⭐ YEGG

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Apt name for a lover   Internetworked   Latter-day dude