When is humor in the workplace appropriate — and what does a little levity add to the collaborative process? Ample research has documented how and when employers and fellow employees appreciate jokes, pranks, and humorous "water cooler" discussions. This case study looks at what might seem a more risky form of workplace humor: job searching with levity. Case authors Anupriya Dwivedi (GSB '20) and Professor Jennifer Aaker detail Dwivedi's job search process during the 2020 global pandemic, and how to roadmap an email pitch using carefully curated elements of humor. Would communicating with levity, and messaging designed to make the reader crack a smile, help her get a foot in the door?