Human conversation relies heavily on conversational implicature, in which speakers convey meanings that are suggested rather than explicitly stated. Although recent large language models exhibit strong conversational fluency, they remain unreliable when interpretation depends on reasoning that integrates social and contextual cues, a process rarely articulated in text. We introduce DRinQ, a benchmark for evaluating pragmatic reasoning about conversational implicature in question utterances, designed to isolate pragmatic variation while holding each question's surface form fixed. To support scalable evaluation, we propose a semi-automated pipeline that produces question-context-interpretation instances with systematic variation. Across evaluations, we find a consistent generation-inference asymmetry: while state-of-the-art models can generate plausible pragmatic scenarios when guided, they often fail to recover the intended implication at inference time. For smaller models, structured prompting improves alignment with human judgments. A comparative writing study further reveals complementary strengths: human authors tend to produce safer, predictable contexts, whereas models generate varied scenarios with interpretations that sometimes exceed contextual support. These findings highlight persistent challenges in modeling conversational implicature and motivate more context-sensitive evaluation frameworks.