This market research aims to investigate the digital information scanning and the internet using habit of Generation Y in Bangladesh, a rapidly developing e-commerce market. It also examines the key variables to optimize digital advertisement for the target group. The study segments Gen Y into two age groups, 18-25 who are students and between 26-35 years who are working, in order to explore the transformation in online consumer behaviour. Most data have been presented according to the segments and gender. The analysis in this study is based on 305 face to face surveys during April-June 2015 using structured questionnaires. This research found that Gen Y with internet access living in the capital of Bangladesh has similar traits as found in many researches focused on developed online market. Facebook is their primary source of information and they have moved away from watching TV. But they are still exposed to the traditional advertisements through billboards and other non-digital media. They are mostly active online on Facebook, Google and YouTube from 5PM to 2AM. This information, along with other findings in this research, provides rich data for advanced targeting variable in Google AdWords and Facebook Advertising. Pop-up ad is the least liked feature by Gen Y. They prefer innovative and interactive ads displaying new product information. They also tend to click on online ads showing discount coupons and similar offers. Ads representing social benefits motivate Gen Y. This study sets a benchmark as it is the first of its kind in the context of Bangladesh. Thus it can be used as the foundation of a longitudinal study on the topic.