Evident in classrooms today, it is not uncommon to have young learners skillful as technology users and game players who enjoy the hardship of taking part in challenging games and competitions, paradoxically, unwilling to deal with the challenges of the writing game. Perhaps it is logical to assume that the most convenient means to engage this group of learners in the writing process is to present them with instructional practices that they deem interesting and stimulating. To put this into practice, this study reports on the work with a digital native in an effort to develop a more positive attitude towards writing and with the ultimate aim of improving his writing performance. The foci of this study is three-fold: it explores the qualities that this learner has and brings to light the challenges he faces in the writing process as well as it looks into potential strategies and methods that might motivate him to become a better writer. Further implications and recommendations are suggested for teachers to engage such kind of learners in the world of writing.