Potential answers for "More rakish"

⭐⭐⭐⭐ JAUNTIER
⭐⭐ DISSOLUTE
⭐⭐ ROUE
⭐⭐ SATYR
⭐⭐ SWINGING
⭐⭐ SPORTY
⭐⭐ ROUES
⭐⭐ DASHING
⭐⭐ LEER

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Chicago setting (Abbr.)   Iron Age people   2400, on the SAT