This paper aims to apply theory of "habitual domains" to analyze the feasibility and effectiveness of "dating simulation" activities among university students. The research project is inspired by John Dewey’s "learning by doing " as the theoretical basis, and the use of "action-oriented learning" approach for the study. The participants, 192 male and female students at A National University in Taiwan, solicited a call for simulated dating partners with specific trip plan, surprise gifts, and chatting theme, via online advertisement, a common way on university campus. After the simulated online dating activities, participants were asked to share their experience by joining a writing competition, or releasing their on-site videotaping record on line, which attracted a variety of local news coverage. Research findings show that" dating simulation "activities can play a positive role in facilitating student communication and interpersonal skills which is preliminary for dating willingness and competence. The theory of "habitual domains" can facilitate "dating simulation" activities, by playing a surrogate role to encourage university students to come out of the "otaku" living style, and participate more in the society.