Virtual assistants are rapidly growing in popularity, triggering businesses around the world to explore their applicability. From a user perspective,, having a conversational interaction with technology has certain advantages, as it is easy to use, hands-free and eye-free. Despite the fact that Transavia already released its first steps with the assistant, there is still minor knowledge about how it can be used effectively to engage with the customer. A techy, social and young customer group - often referred to as Generation Z - is interacting with technology and brands in a very different way than Millenials. As a starting point, a preliminary design goal is formulated which links the technology and the user to an early touch point in Transavia’s customer journey: ​“Design a virtual assistant for Transavia that offers added value in helping Generation Z with finding and/or booking flights”. The contexts of four aspects are analysed: business, process, user and technology, which together lay the foundation for the subsequent user studies. The studies show the flight finding and -booking behaviour of Generation Z, as well as their current and preferred interactions with virtual assistants. Based on the outcomes the witty assistant ‘Tracy’ is conceptualised and piloted using the Google Assistant and Lenovo Smart Display. Tracy focuses on the moment right before booking called pre-booking, and recommends Generation Z affordable trips based on their availability. Alongside user tests the prototype goes through three iterations to optimise various aspects of the design: tone-of-voice, product personality, content and conversational flow. The final design is intended to be feasible for a short term release, and proved there lies true potential in using a conversational interface to engage with Generation Z in the pre-booking phase. Finally, recommendations are proposed for Transavia to support them when continuing with either Tracy or with virtual assistance in general.