Entry 1 sense Webster, 1913 Flirtation /flẽrt-āsh'-ən/ · Flir·ta·tion · IPA /flɚˈteɪʃn̩/ 01 n. Playing at courtship; coquetry. 1. Playing at courtship; coquetry. “The flirtations and jealousies of our ball rooms.” — Macaulay.