The situation of an incarcerated loved one is no less worthy of love, hope, encouragement and prayer, so I strongly suggest we start there. If we pray for our loved ones, those who are incarcerated and the broader family of blood, law and choice who have been affected by the incarceration, we can avoid a lot of regret. Encouraging our incarcerated loved one to pray for us can open a heart. Pray without ceasing with every decision to made, every word written or spoken. Keep praying.
There are a lot of practical matters to consider as we maintain our relationship with loved ones who are incarcerated. Here are some suggestions:
1. Find the website for the facility where your loved one is incarcerated. There will be Q&As or tabs that will provide specific rules about correspondence, gifts, commissary and visits. Check back often, particularly before visits since it is bad for everyone if you travel a long way and then find there is a reason you cannot visit. Even when you try to follow the rules it is easy to assume something or interpret something or miss something that causes delays in letters or approved items getting to the inmate or derails a visit. Expect it. Trust God will get things through according God's ideas of what is needed. Don't waste time and energy with "shoulda's, coulda's, woulda's" especially when it comes to the prison and jail situation.
2. When corresponding, speaking or visiting an incarcerated loved one, it is a fine line between sharing honestly and emotional battery. That is where prayer can help so much so in avoiding the pitfalls of resentment, hopelessness, fear and anger which are particularly destructive when wrapped in self-righteous, judgmental sniping disguised as 'just wanting to help.' If you are struggling with this and need to have a serious talk about challenges ahead, I would encourage you to write it out, even if you expect to have a conversation, and work it over, pray over it to make it as clear, yet gentle as possible. If it is going to be particularly challenging you could even practice the conversation with a trustworthy person of maturity and judgement. I don't presume to assure that it will not still be difficult for the incarcerated person, but it will definitely help YOU.
3. Don't tell lies or even "shade the truth." This does not mean exploring every tiny fear or wildly imagined possible bad outcome. With lots of time on their hands and humble jobs of work they can fret into a panic attack without any assistance. Instead speak of your trust that God will see you through, or speak of the plans you have for addressing the challenge. You will hang up the phone, walk away from the visit or lay the letter down and turn to many matters that are pressing or pleasing or soothing while your incarcerated loved one will be fighting the demons of frustration, guilt, hopelessness and the demands of the prison schedule. When they ask questions, give the most honest and kind answers you can.
4. Always remember that what you think just doesn't count for much when dealing with prisons. They see every form of foolishness, evil, creativity turned to danger, abuse, injury and death. When they say "don't send books" (as one facility in my personal experience did) you can bet their diligence may save YOUR loved one from injury from weapons in the spines or smuggled pornographic pictures or pages soaked in drugs hidden in books gifted to jails and prisons. Although your motives are pure and you are not doing that, if someone does that and it is your loved one that is injured or tempted or blamed....well I know you don't want that even though the rule bugs you.
Most of all, cover all communications and decisions in prayer. God loves you and is caring for you and your loved ones day and night year around. God is trustworthy.