Would you be concerned, feel a little skeptical, or feel like you're walking on thin ice?

So I understand that people need to feel reassured to make themselves feel comfortable about a situation or with themselves. But when they overdo it to the point where one feels like the person comes off as skeptical in conversations where communicating with them feels like a quiz/test to the point where at times I would have to think about how to reply based on them sharing with me a conversation they had with someone they felt like it didn't go well. Majority of the time I have to reply back with humor, emojis, or nothing at all because it seems like they hold on or are keen to every little thing said or done that it might be best to communicate with them less and continue with my day minding my own business.