The best way to edify a man is, most often, to facilitate his monologue on his emotions. Two years ago, I wrote a post on the importance of having the other guy do most of the talking. This post is more on how to encourage emotional expression.
Here are a few questions you can insert during short pauses in his monologue. Asking thoughtful questions is a wonderful way to take any discussion to a deeper level. Men usually have little trouble going deeper into mechanical explanations but are often almost mortally scared to go deeper about emotions. Asking questions that call for emotional feelings and expressions signal that you are free and open to these things. It just may help him get the courage to share it with you. That will also help free him from his emotional lock-up.
- How did you feel when [name] said that? or How did you feel when [name] did that?
- How do you guess [name] felt when saying that? or How do you guess [name] felt when doing that?
- How did you feel when you said that to [name]? How did you feel when you did that to/for [name]?
- What emotion were you trying to convey when you said that? Had you thought about the emotional impact of what you said to [name]?
When you ask these kinds of questions, you help facilitate his monologue on his emotions. When we ask someone questions like this, we need to think about the emotional impact on him! This is very important.
For more on emotional intelligence, see this post by Eric Barker. The book on which Eric based this blog post has an excellent chart of 100 different emotional words. It has four general categories. I would post it here, but that would be a copyright violation. You really might want to get the book to help both yourself and others expand emotional intelligence.