> It takes me about 3-4 months of being around someone regularly before I'm able to hold a conversation that's more than direct answers to direct questions.

I had trouble with this for a time, I just tried to take my answers a tiny step further. If someone says "Wow, it's cold outside", instead of just responding with a "Yeah, it is cold", try and add your opinion on it. "Yeah it's cold, I love this weather", or "Yeah it's cold, I hope it gets warm for the weekend, because I was planning $outdoor_activity". Anything along those lines will make you seem more personable.

This is exactly how to start a good conversation. People make small talk as a way of signaling that they'd like a conversation. All you have to do is say something that keeps the conversation going. The best things to say are positive statements about how you feel or what your background is because it gives the other person a chance to relate to you.

Interesting.

I tried this for a while, then for some reason got really conscious that the over-use of "I" and "me" in the response made me sound too self-absorbed.

So nowadays I'm usually slowly thinking through whether a statement like "Wow, it's cold outside" warrants mere concurrence or greater engagement.

I honestly suffer the same thing. I think deep down, it is a character flaw for sure. Something egotistical and asshole-ish.

Interestingly, I’d say both apply to me and it’s actually about the same time period, too.