The arrival of Internet of Things (IoT) overcomes limitations of time and space by providing ubiquitous accessibility of its products. Design and HCI research are challenged by an increasingly complex network of diverse types of interaction. To design pleasurable user experiences (UXs), new models need to be developed for emerging IoT products as previous models for conventional products might not be applicable anymore. From a human-centred perspective, this project investigates how the pleasurable UXs will change after a product develops into an IoT product. The project aims at understanding the attributes of IoT products that might contribute to understand the future relationship between users and IoT objects. The project applies UX theories by Jordan (a hierarchy of consumer needs, 2003) and Hassenzahl (top-ten psychological needs, 2010) as theoretical guidelines. These theories classified the contribution of human factors to design pleasurable products and agreed that the enjoyments from the psychological level are at the top of UX. The project uses two online questionnaires to collect data on 1) the UX of Smartwatches and 2) conventional Wristwatches (digital and analogue), in order to reflect on the influence of IoT products on the pleasurable UXs. The results show that the UXs of IoT Watches and conventional watches were not significantly different in terms of the four kinds of pleasure as proposed by Jordan; however, IoT products and conventional products did appear to influence some items in top-ten psychological needs differently.