TL/DR: One of my needs in our relationship is going unmet: the need for engaging, thoughtful conversation. I truly believe my partner is capable of this, but hasn't been in an environment where he was encouraged to have more than superficial discussions. How can I help him build his conversational skills and confidence?
Example: To try to clarify what I mean by thoughtful conversation, I'd be talking about things like ruminating on an interesting movie we watched (how does it reflect current society, are we going that direction, which character was fascinating and why, was the story arc good or what plot armor was there, etc) versus walking out of a movie and having it left at "I liked that movie."
I've tried model this with him to some extent with conversations about football, which he is super knowledgeable about where I know only the basics. He'll mention something in response to sports radio and I'll ask something like "Oh? Which position was that?" He'll tell me which one, then I'll ask something like, "What does that position do again?" He'll go on in some detail until I understand the gist of it and then further engage him with a question like, "Why is that guy not a good fit for it?"
This is the kind of conversation I'd like to have, but about other topics as well, not just football. And instead of being the one engaging every time like above, eventually I'd like him to be able to engage similarly with me, even about potentially unfamiliar topics. Most of our conversations just feel like typical small talk ("how was your day," "what should we eat today," "want to do anything this weekend," etc).
To try to summarize the example, I'd like it if when in a conversation he would:
Provide more than one word answers when I initiate a conversation (responses less like "ok," and more like "oh, I agree/disagree/don't know because xyz")
Be open to discussing in more detail than generalizations ("I liked that movie, but I would have liked it more if..." versus "It was good.")
Be willing to listen and engage on less familiar topics (If I mention something like, "Huh, this article mentions a new technology for doing xyz," answers less like "Um, ok... That's random" and more like "Oh yeah? What's new about it" or "Oh, how would that work?")
Extra Background: This info may not be necessary to basic advice, but may also have details that could help. Feel free to skip it.
I've been dating my fiance, who I love and who I know loves me deeply, for about a year and a half. We've been living together for half of that time now. We got engaged the week before I graduated from grad school with my MA this past May. It wasn't out of the blue, as we had mentioned getting married before, so of course I said yes. In the past couple of weeks, my feeling of closeness to him has declined noticeably.
In general, I'm the kind of person whose mind is constantly churning through things, but who has to make an extra effort to identify my feelings, so I spent a couple of weeks in a confused state of low morale before I could identify why I was feeling so badly and figure out the cause. I didn't feel like I could truly connect with my fiance emotionally. We had a discussion about this (that went much better than I had dreaded) and together came up with some actions items for each of us that we thought could help, including me being better about expressing my needs unambiguously and pointing out behaviors that cause the disconnect when they happen instead of letting it build up.
He also shared what he called his greatest fear: that I would realize I was too smart for him and leave. I reassured him immediately and emphatically that this wasn't the case, that I loved him, and that he is also an intelligent person and possess more intelligence than I do in a number of cases (emotional intelligence comes immediately to mind).
I understand, though, where this fear comes from. He was a college drop out; I just obtained my MA. His family do not have any higher education; mine almost all do. Through our mutual hobby, we're surrounded by bright people who are almost exclusively male. I love getting into the weeds on a variety of topics with them, and there are several that I can hold really good conversations with easily. In thinking through my fiance's fear, I also realized that since I graduated my master's program, I have been turning more to these friends for that kind of engaging conversation, probably because I'm not getting it through classmates and professors any longer.
This realization caused a bit of a personal panic in me because I was faced with the question "Is this kind of conversation a need of mine in a romantic relationship?" I'm afraid that if I'm honest with myself, the answer is probably yes. It's nice to get this need met from friends and colleagues, but I'm extremely worried that if I don't get at least a little bit of it from my husband-to-be that I will drift away from him. I can see how the lack of this kind of conversation went unnoticed until now with almost all of my intellectual energies focused on graduating and breaking into my career, but I'm kind of kicking myself for not realizing it sooner because of how deep into the relationship my fiance and I now are.
All this backstory leads to the question: can I help him develop the kind of skills that would help him fulfill this need of mine? How specifically would I go about helping build those skills? He was a straight-A high school student who was bored by school. He's a capable problem solver (I see this in action all the time). I just think he's never really gotten his sea legs regarding his own intellect or expressing his ideas. He's also told me he thinks his communication skills could improve. Additionally, I would bet that he probably feels intimidated by me (and some of our mutual friends) since having more substantive conversations is my default setting.
Research: I did some searching and found this answer that seems somewhat related, but not quite the same. In that user's instance, it was always the same few topics, but for me it's more of a depth question than a topic question.