I feel like I’m pretty decent at carrying on light, casual conversations, but I struggle to take them deeper. I end up mostly repeating a script of things I know to say with small variations. There are people I see regularly here and there who I feel I should know better by now but don’t. How could I go a little deeper with out talks without being weird?
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So I’m working on this as well but what I think works is this: After the small talk script, when I’m a little more relaxed, I try to open up a little. So to some I talk a little about what is currently driving me, for example that I would like to get out more and am looking for people to play Card games or pen and paper with. From my experience this deepens the connection with them, as they see you as a 3 dimensional person, that has issues and goals they are working on and not just some small talk robot. But you have to find a middle ground between complete openness “I’m really down and need to get out of my flat because I can’t stand it in there alone anymore” and the small talk. Finding this golden middle is not easy but if you do it right then it won’t be weird and you will have left the small talk behind. Also a good tip is being a strong listener when they tell you something about themselves that goes beyond small talk. Listen, ask questions, give the impression that you are interested and want to know more and leave the level of meaningless conversion to really talk with someone. But this is just my opinion…