Entry 2 senses · 2 variants Webster, 1913 Painstaking /(pānz"tāk`ĭng)/ · Pains·tak·ing · IPA /ˈpeɪnˌsteɪkɪŋ/ a. n. 01 a. Careful in doing; diligent; faithful; attentive. 1. Careful in doing; diligent; faithful; attentive. 02 n. The act of taking pains; carefulness and fidelity in performance. 1. The act of taking pains; carefulness and fidelity in performance.