Aw, I understand now. This sounds like the kind of thing I would worry about, I am very introverted and uncomfortable in those settings. I'd recommend you go to the event or find another one like it your T won't be at. The best advice I ever got about making small talk when I don't know anyone is to ask people questions, it works like a charm most of the time since people love answering them.

I would talk to your T about it. In my lay persons opinion this event is bringing up some legitimate fears of yours that can/should be explored, this is good therapy stuff. The awkward bit about how you know where her daughter goes to school etc. is not that weird really. I know what car my T drives. I guess it would sound odd in a normal conversation, but this is a conversation with your T. It doesn't make you sound like a stalker is what I'm getting at