Dear Dan, I just read your post on spiritual friendship. I will be going for spiritual direction soon. I have some 
concerns. From what I’ve been reading, and what I have been feeling (fear, anxiety, restlessness, doubt if I should go ahead), spiritual direction is a very intensely personal thing I have to go through with a stranger (a priest alright) if I want to improve my spiritual life, but then, I cannot be personal but treat this as a purely professional transaction the way we can’t be personal with our doctor who would probably have seen most of our physical selves. Am I right in thinking this?
Being human, I would find it hard not to be at least a little personal –friendly, that is–to someone who would be helping me a great deal in the most important part of my existence on earth. Other than shaking hands and communicating regarding our SD meetings, what would be considered overstepping my boundaries in the relationship with my spiritual director? We give gifts of appreciation to friends; would it be offensive to do the same with my SD? If my SD can ask questions about my personal life (family, etc) outside SD, I expect not to be able to do the same, am I right? I just want to be respectful. It’s very hard to find a good SD and I wouldn’t want to offend one I have right now. I am married woman by the way.
My second concern is, do I talk about previous sins that I have already confessed, in our forthcoming SD? I will be going for SD within a couple of months or so.
Dear Friend, you are asking good questions. I recommend you read my book Navigating the Interior Life – Spiritual Direction and the Journey to God. All the proceeds from those books distributed through our site go to help those who can’t afford to purchase faithful spiritual literature. In it, I outline and answer all of the questions you ask here along with many others. In the meantime, here are a few quick answers to your questions (we also have an endless number of posts on these topics under the Spiritual Direction category):
Question: Should I give gifts to my spiritual director?
Answer: Absolutely as you are led by the Holy Spirit and by charity in appreciation for their assistance.
Question: Am I right in thinking I can’t be personal?
Answer: No. You can and should be personal. The post on spiritual friendship you read was meant to make a distinction between spiritual friendship (low accountability) and spiritual direction (high accountability among other key distinctions). The post was not meant to discourage a personal connection with a spiritual director. That said, a good director will generally keep a healthy distance in order to allow for objectivity and appropriate boundaries. A good directee will avoid pushing these boundaries.
Question: What is “overstepping my boundaries” with my director?
Answer: To cover the obvious first, any expression of intimacy, emotional or physical, that should be reserved for your spouse alone (or would-be spouse), would be an overstepping of healthy boundaries. As well, we need to respect the fact that our director needs to maintain an objectivity that can rarely be achieved when we are overly friendly in the relationship.
Question: Should I ask my director about their family life?
Answer: No. Good spiritual directors are generally extremely busy. You should be ready to sit down as soon as you meet and pray, and then begin to seek direction about your progress in prayer and virtue.
Question: Should I talk about previous sins already confessed?
Answer: It depends. If you are struggling with breaking a pattern of sin, this would be an appropriate topic of conversation in spiritual direction. Also, you might need to reveal important instances or patterns of past sins with a director who may not be familiar with the history and state of your soul. Let your director lead you in what you need to reveal.
