In order to improve user experience and to foster novel ideas, some voices in the HCI community have argued to break fundamental design rules, an approach well known in the art community. In this paper, we use this radical approach to design a playful mobile chat app called Chachachat, which allows users to send colorful 3-phrase messages from a limited set of phrases taken from dating websites and encourages intimate messaging with strangers with no possibility of meeting offline. We also present a case study of the usage of Chachachat in the wild over a period of six months and discuss ethical issues.