This study investigates and compares the effects of incorporating jokes in face-to-face interactions between employees and customers on the customers’ shopping experiences in two different settings i.e. small retail outlets and stores in large shopping malls in India. Two separate studies were conducted in the year 2023-24, involving a total of 578 participants from four retail outlets and four stores from one large shopping mall in Delhi. The findings revealed distinct shopping experiences among customers in India. In the retail outlets, customers reported higher levels of satisfaction when employees used jokes during their conversations. Conversely, in large shopping malls, customers expressed lower levels of satisfaction when jokes were incorporated. Additionally, the results indicated that humorous interactions led to increased sales in retail outlets, but had no impact on sales in stores at large shopping malls. Furthermore, the perceived relevance of jokes differed between the two settings, with retail outlets experiencing an increase in perceived relevance, while those in large shopping malls showed no such effect. The study also demonstrated that older customers in retail outlets tended to develop a stronger emotional connection with employees when jokes were included in their interactions. On the other hand, customers in large shopping malls preferred to engage in shopping activities without any interference from store staff.