In the fast-paced and customer-centric hospitality industry, where employee engagement and proactive behavior are critical for service excellence, organizations face the challenge of fostering a motivated workforce. This paper explores how integrating play into work through Playful Work Design can enhance employee engagement and taking charge behaviors. Drawing on Self-Determination Theory, we propose a process model wherein playful work design, specifically designing fun and designing competition, positively influences employees' taking charge behavior through enhanced engagement. Furthermore, we explore the moderating role of contrived fun—fun activities consciously organized by managers—on the relationship between playful work design and employee engagement. Using primary data collected from 325 employees and their immediate supervisors in the hospitality sector, our results offer industry-specific insights into the direct and indirect (via employee engagement) effects of playful work design on taking charge behaviors. Moreover, we found that contrived fun moderates the impact of playful work design on engagement. Our findings not only contribute to the advancement of hospitality management literature on playful work design but also provide practical insights for hospitality managers seeking to cultivate an engaging and proactive workforce. We illustrate how hotel staff can leverage playful approaches and use friendly competitions to enrich interactions and enhance service delivery.