This paper is an exploratory study that attempts to analyse the shopping orientations of two of the most influential generational cohorts – Baby Boomers and Boomlets. The purpose of the study is to help retailers draw appropriate strategies in a highly competitive environment. The two generations together have the highest spending power and is therefore important to retailers. One of the questions the study attempts to answer is whether shopping is primarily a family activity in the Emirate of Dubai. The findings of the study will help retailers to organise store atmospherics, choose appropriate merchandise and store location etc to encourage maximum store traffic. A survey of Boomlets and their Boomer parents was conducted using an instrument with 15 questions. The results were analysed using frequency and cross tab functions in SPSS. The findings point out that there is a perceivable difference in the shopping orientations of the two cohorts and so mall managers and retailers have to engage in micro merchandising. There has been no study of generational cohorts in the region and hence this study is of great value.