That’s fine, but I assume you mean that you’re not sure when to say something more substantive than a simple affirmation that you’re following along. A couple of other tips I’ve picked up that help with this:

After implementing what you’ve said in the past couple of my interactions, I noticed that people were more likely to smile and attentively listen after they’ve shared something themselves. Eliciting that initial interest from the other person removed a lot of the awkward silences, as it was filled with them talking more than myself. As I’ve been focusing more on what the person emphasizes, I’m able to find out more about what excites them to talk about, so I’m able to draw more attention to their interests and make them feel heard. Very good advice here.

Generally try to ask open ended questions rather than yes/no questions. And remember my first tips that the question you ask is also a way of conveying where you want the conversation to go. So if you don’t want to talk about your own parents, maybe it’s better to ask about the beach. And don’t be afraid to say “me too” and then if they say something like “really?” then it’s your turn to talk for a bit as you relate the thing you have in common with them.

To solidify this advice… Are there any “baskets” that questions generally could be sorted into? The open-ended type sometimes falls flat if I ask it from the “wrong” basket. Exactly as you mentioned with not wanting to talk about your own parents, but asking about them anyways and then not having much to say directly afterwards. Not to neg on details, but would it be unhealthy to think a certain amount of steps “ahead” in a conversation? This has been on my mind lately, but I’m not sure how to describe it other than I’d like to engage the person and get them to think about things rather than be a captive listener or have them monologue about themselves.

I feel like I don’t understand eye contact or body language too well. We all know the awkward feeling of seeing someone far away in a hallway. I’ve never quite got this one down… If I know the person, it’s usually okay to make some strange handmotions and tease a bit as you get closer. But sometimes, I can tell the other person doesn’t want to look at me, but will raise their head to say hi as we are within 5 ish feet of each other. A strange autistic detail, but I just want to be more charismatic in general, and appreciate you taking the time to write these comments!

Just cross posted! Hopefully that will get this idea more engagement.

Will do! Send me a DM if you’re interested in having a quick chat.

This is great advice! I’ll try to implement it over the next couple of times I’m chatting with these same people. Oftentimes, I find it hard to gauge what the other person might “want” to talk about. This can be challenging with people who are more shy or not necessarily big conversationalists from what I’ve experienced.

My follow-up would be… How do you engage in a dialogue? Do you adhere to any principles as to how long you are talking, the uniqueness of words that you use to describe your ideas…? How do you balance what you’re going to say with active listening? Because sometimes I feel like I attentively listen TOO much, and I’m just there nodding and dispensing a digitized voice-line of “wow!” “awesome” “fun” “cool” “Oh that’s interesting” and so forth…

Amazing dumpster find! How long did it take you to fix?