Twenty years inside changes a person in ways that are not always visible on the surface, and understanding that context is the foundation of everything else.
When someone spends two decades in prison, they spend two decades in an environment where showing emotion is a liability. Appearing vulnerable or soft creates problems. Keeping feelings locked down is not just a habit, it becomes a survival mechanism so deeply ingrained that it does not simply switch off when the sentence ends. What you are likely experiencing, the difficulty getting through, the emotional distance, the guardedness, is not a reflection of how he feels about you. It is the residue of twenty years of necessary self-protection.
Trust is the core issue, and trust takes time to build on both sides. He is relearning what it means to exist in a relationship where honesty and openness are safe. That is not a quick process. Pushing too hard or expecting emotional availability before he is ready will close things down faster than almost anything else.
Patience is not a passive thing here. It means showing up consistently, keeping your word, not reacting to the walls he puts up as personal rejection, and giving the relationship room to develop at a pace that feels safe to him. Over time, as trust accumulates through small consistent actions, the communication tends to open up on its own.
If things feel stuck after a genuine effort, a counselor with experience in reentry relationships can provide tools that make a real difference. There is no shame in getting outside help for a situation this specific.