How to know when I am revealing information that could be damaging to me?

So, different people have different responses to things. Some people, for example, are happy and congratulatory when I tell them something good happened to me (does not have to be big, could be as simple as I went on a fun trip or got a cool item).

Others respond with apathy. They might just nod or say “ok.” I am generally ok with these folks.

The worst group though are those who respond with envy or anger, sometimes making snide comments like “Oh, you think you’re so cool, huh?” or “What’s the big @$*&% deal?” They might also use body language, such as frowning or rolling their eyes or giving me a stink eye. These guys might subsequently give me a hard time about things when I see them again in the future (might or might not be caused by envy, but I can’t think of any other reason, as I have done them no harm).

Now, I usually keep to myself and won’t go around bragging about myself. While it is possible to avoid members of the last group once I have encountered them, there is no telling which group a stranger would belong to until I have actually spoken to them. I know the saying “Don’t talk to strangers” but that is hard when said strangers might be your new classmates or coworkers.

I can give blanket answers to small-talk questions as in (Them: How are you? Me: Good.) but that does not lead to much conversation. I don’t think lying is the way to go either as it is simply hard to keep track of lies, without even discussing the morality of lying.

So, what advice could you give me regarding this? And if I am meeting someone for the first time and they ask me “What did you do over the summer?” should I tell them my fun adventures or go with something more lame like “I just chilled?”

So,