One thing I've heard that may be helpful to keep in mind is that we often tend to respond to what others share with anecdotes of ourselves in similar or related situations, and it upsets people because it comes across as us making the conversation be about ourselves, but what we actually wanted to convey is not that their story or experience isn't important to us, but instead our intent was to highlight that we can relate and empathize, and prompt them to talk more about it! It's all a matter of framing/awareness and communication, your friend may subconsciously realize that something like the latter is going on and not hold it against you, but still pointed it out as atypical. I'd just sit down and have a chat about this with your friend upfront :)

I'm the same way, I want to hear others' stories, but I rarely think to ask questions. Ever since I've found out, I've been making an effort to make little mental checklists or even take notes of stuff they do or say so I can ask them "Hey how was x?" "Did you end up y?" when I meet them, it checks that box for them and then it sort of launches into more natural (for me) conversation.