My comment is going to risk psychologizing you and may end up being unwelcome, but since you've opened up on here about your experience of getting less insecure, I don't think it's out of line. Apologies in advance if it is for you.

Something pinged when I read this line:

You still asked probing questions like “Why did you quit your job?” and “What did you think of your manager? I hear they don't have a great social reputation.”

What pinged is that these don't register to me as probing questions at all! These seem like normal attempts to learn about someone by asking about what is, for most people, a very large part of their life: work.

Then I got to this line:

In the past, I would have felt forced to answer your questions. But I’m sure you can remember how I responded when we spoke again: “Mm, I don’t want to answer that question”, “I don’t want to gossip”, and even a cheeky, “No comment :)”

To me these still read like defensive, insecure answers. Perhaps less insecure and defensive than totally shutting down and running away, but still refusing to engage in what most people would consider socially acceptable and normal questions to ask. If someone kept giving me answers like this my first thought would be "oh, I see, this person doesn't really want to vibe or converse and is making me do all the social labor".

But it seems I unlearned most of mine. I don’t encounter situations that make me anxious in that way anymore, and I can’t imagine any new ones either. Rejecting others (and being rejected by others, same thing) has ceased to carry much unnecessary emotional weight.

Maybe. Or maybe you found a new strategy to suppress your anxiety so you don't have to feel it. I don't know; I don't know your mind. But what you've described pattern matches to a kind of bypassing that is a healthier coping strategy that what you were deploying before, but also doesn't fully address the anxiety.

Again, sorry if this was more pointed a comment than you were hoping for. I offer it only in the spirit of saying the sort of thing I would have liked to have had said to me if I were in your position.

[-]Chris Lakin1y30

What pinged is that these don't register to me as probing questions at all! These seem like normal attempts to learn about someone by asking about what is, for most people, a very large part of their life: work.

Partially I began to agree after the shift, partially I guess there's more context that I haven't been able to communicate through text.

To me these still read like defensive, insecure answers

What might say if you felt like that in that situation?

Thanks for commenting, I'm not concerned

[-]Gordon Seidoh Worley1y40

> To me these still read like defensive, insecure answers
What might say if you felt like that in that situation?

It's tough to say without more context, but if I really felt like I couldn't say much, I'd probably at least give a "nothing burger" answer like "oh, I was ready for something else" or "we got along as best we could". This might feel like the same thing but the vibes of it are different. A polite avoidance of the question while still engaging with it rather than a more direct shut down.

But of course in most cases I'd probably say more because it would be safe to, up to whatever seemed like a reasonable amount of information to disclose under the circumstances.

[-]Chris Lakin1y20

That seems more avoidant to me than what I said haha.

Also, I fully expected this person to ask questions for more detail if I had said what you suggest.

[-]cyber-chris1y32

On the other side of this, after realizing that people were willing to say no, I realized I could freely ask a lot more "spicy" and interesting questions to people.

At the time, professionally, I entered a rather cagey/secretive finance industry so it was liberating to realize I could ask tough questions, and at worst higher-ups would give me a knowing nod coupled with a "I'm afraid I can't answer that one".

(Admittedly, this started to bleed into Slytherin-level tricks where I tried to watch for how quickly someone responded or denied. I certainly avoid doing that to random folks at a party, though!)