I often keep brooding on whether to do certain things for a long time after and during interactions. Sometimes I feel like I have become the annoying dude who has asked too many questions and have annoyed the heck out of person I just met and.... sometimes I feel I shouldve talked more. I guess it may be either one or a mix depending on the situation.
The other day, I talked for like 10-20 seconds with someone after a greeting about work-related stuff and I was asking why they were absent and they mentioned one of their siblings passing away and I immediately (naturally) withdrew and didnt ask why or how because she was like my boss and didnt want to open a discussion she didnt want to talk about. But later on I felt constant regret and kept considering asking her somehow while I was working there but the other side of me was like logically thinking 'maybe she doesnt want it brought up. don't be a d1ck' and this boggled me the whole day. I was also extremely interested on why but I dont know if I was being selfish for my own interest or concerned or both. And I felt like I may come off badly if I brought it up
Theres always this conflict.
Sometimes its less severe and I just end up thinking the persons annoyed because I interviewed him too hard. Those are usually less important since its a cold approach