If you have been involved in the pastoring / discipling / teaching / catechizing of new professors of faith, what principles, if any, have guided the degree of familiarity with which you fellowship with them?

To keep it simple, let's assume only same-gender fellowship; let's also assume you fully understand doctrinally why not all may persevere.

More specifically, do you tend to be more familiar with new believers, hoping to tenderly encourage them as they begin walking in faith, or do you tend to be less familiar, not wanting to give false assurance to those who will fall; or some combination, or none of the above? Has the potential of emotional sorrow of lost fellowship when someone has fallen away affected your approach? Has anyone struggled with this?

In Christ,
Paul S