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Then I asked her if there were any highlights and she simply said “no”. I was getting those vague, short answers again so I tried asking more questions and asked here what kinds of things there are to do at the video game convention she attended and and how many people were there. This was when Jessica seemed to get a little irritable. Jessica sort of responded to me like I was stupid....
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Those vague, short answers are social cue. They are a signal. They mean “Hey, I don't want to talk about this now.” She got irritated with you because you missed that signal and pressed ahead with more questions. Something similar apparently happened when you asked her about youtubers.
Perhaps this is why Jessica feels nervous around you. But whether it is or not, in my opinion you would be wise to back off when people signal to you that they don’t want to speak about something.
Given that she can speak freely and naturally with a manager, I am skeptical that she has social anxiety.
You can’t “make” Jessica feel comfortable around you. However, you could change your style of questioning and see whether or not, over time, that makes a difference in how she reacts to you. You could tell her that you’ve been thinking and you realize that sometimes you ask too many questions. You could apologize for that and promise to do better.