I once read that the official position of Judaism on people who wanted to join that faith was to deliberately discourage them three times before accepting their wish to become Jews. Does Orthodoxy take a similar approach? That is, does it encourage other Christians to find a “working truth” (silly as that might sound) in their own denominations before considering Orthodoxy?
Furthermore, I understand that the Orthodox Church does not carry out missionary work among non-Orthodox Christians, and that it encourages (or perhaps requires?) non-Orthodox who wish to marry Orthodox to join the church. What is its stance, however, on individuals who want to join simply of their own free will?
While there is no formal point by which prospective converts are discouraged three times—a Jewish practice to which you refer—those wishing to enter the Church should not do so lightly and should only do so after a period of preparation and catechesis, coupled with the opportunity to identify with the Orthodox faith community. This period may vary from person to person, depending on their circumstances, their fears and concerns, and so on.
Since conversion involves a change of heart and mind, it is more than a matter of intellectual assent.
It is only my personal opinion, but if one approaches Orthodox Christianity as an “option” or as a means of “running away” from something or someone else, rather than as “The Way” [as opposed to an “option” or “one of many ways”] which demands one to “run to” Christ, one should not seek entrance into the Church. Until an interior change is experienced, no genuine conversion takes place.
There are those who would cast Orthodoxy as a “non-missionary” Church. Such is not the case. As Fr John Meyendorff once wrote, “when the Church ceases to be missionary, it simply ceases to exist.” While the Church does proclaim the Gospel to any and all who would listen and receive it, it does not purposely seek to encourage or coerce others to leave their faith communities. The Church attempts to “speak the Truth in love” and invites others to accept its teachings, experience, and life. While the Church would discourage proselytism, it is most open to those who are seeking the historic Church and the way of life it offers.
As far as marriage, it is not true that a non-Orthodox who wishes to marry an Orthodox Christian must first join the Church. An Orthodox Christian may marry a non-Orthodox Christian in an Orthodox marriage ceremony only if the non-Orthodox party was baptized with water and “in the Name of the Father, Son, and Holy Spirit.”