Marriage is one of the most important topics in the education field since life in this world is structured by interaction among families and between families and other social institutions. Dissatisfaction and unsustainability of marriage have led the urgency of premarital education in various countries. The problem is that the spread of virtual reality has made marriage itself to become more complex and experience reinterpretation and reconfiguration, moreover with the emergence of new kind of marriage in the digital era, i.e. virtual marriage. Everybody who has observed, known, or even tried, certainly asks the question, “Could (or: should) I accept virtual marriage?” . This study was aimed to investigate the role of tolerance of ambiguity and illusion of intimacy in online dating in predicting the acceptance of virtual marriage. There were 420 adolescents and young adults (212 males, 208 females; Mage=21.10 years old, SDage=1.459 years; 338 students, 82 employees or entrepreneurs) in the Greater Jakarta, Indonesia, participated in this study. It was found that the acceptance was not predicted by the ambiguity tolerance, but by the illusion of intimacy in online dating. The psychometric issues, substantive discussion, and recommendation are presented at the end of this article. The trend of virtual marriage should not be allowed to roll away, by autopilot, without loaded by strategies in designing an online game as one of the pivotal educational technologies that needs to shape appropriate character and attitude for it.