How to discuss engagement/marriage with my boyfriend?

My boyfriend and I have been in a committed relationship for two years now, and we have discussed wanting to spend our lives together, but briefly and not in a ton of detail. I have told him that he is the guy I want to marry, have kids with, and grow old with. He reacted well to me saying this and said he could definitely see himself marring me he just hadn't thought about it with any certainty before I said that. It doesn't shock me that he hadn't thought about it a lot, he's very about worrying about today and we'll figure out tomorrow when it gets here, which I highly admire because I am in contrast a planner. However, his figure out tomorrow when it gets here mentality makes things like engagement, marriage, and our future hard to discuss. I don't want him to feel I am trying to force him to do something, or plan everything out, but I would like to discuss it with him. I don't want to know, the exact, time and date of when he's going to propose but I would like to know he is thinking about it, and even planning it. Since I told him I wanted to spend my life with him, he has asked me what my favorite gemstone is (since i'm not a big diamond fan, which he knows). I'm not positive if he remembers but I have told him that the only jewelry I really wear are rings, and he has already gotten me a "i love you ring". He has also mentioned that one of his favorite moments he's spent with me was meeting my parents. This is odd for him to say because though he enjoys spending time with my birthmom. My mom and dad are a little older and kind of awkward as they start really weird conversations or talk about things that no one can relate to, so he has never really enjoyed going to family gatherings with me. I'm just wondering if these things mean anything or if I'm over thinking it. How do I get him to discuss engagement/marriage and our future?