When trying to break into a new social group, how can I gently dissuade someone in the group from isolating me and asking me question after question?

Question

I went on a social outing to a pub. I signed up to this social outing because it was in my area and I thought it would be fun and maybe I could make some friends. This person messaged me through the website I signed up for this outing beforehand and said he was looking forward to seeing me. I said you too (just being polite). I actually went to this outing because I wanted to, not because he was there, because I want to make new friends.

We were all talking, as in group talk, taking turns just shooting the breeze, not talking about anything in particular. And then one member of the group left the venue, and this person moved to sit next to me and started asking me questions one after the other. He seemed to know things about me that I hadn't told him, and I asked him how he knew these things, and he said he'd looked at my profile. So for example he said "What are you doing for the rest of the day?" And I didn't say much, then he said, "Writing?" And I said "How do you know that?" He paused for a moment and said "I looked at your profile."

At that point I felt creeped out (it was an involuntary response) and started to grow uncomfortable in the face of his constant questioning. He kept up with what pets I own, where I grew up, what I do for a living, etc. It was making me uncomfortable. He was staring intently at me and the other people in the group were talking amongst themselves so he had broken us off from them.

So I gave very short, one word answers. He kept going, though, so I tried flipping it back at him immediately, i.e. if he asked 'do you like such-and-such?' I would say 'well, do you like such-and-such?' But he kept on with his questioning so I stared at the TV away from him. Then I thought this might seem a bit rude, so I focused my attention instead on someone else in the group who was talking to another person, and then he did too, and he finally stopped asking me questions. We all left soon after that so I was able to avoid being questioned by him any more.

Later on after we left he sent another message saying he enjoyed seeing me and looked forward to seeing me again.

I don't really know him very well. I only met him once before. I have no idea what he's like; I'm sure he's a nice enough guy, I just really hate being interrogated. If anyone did that to me I would instantly find them repulsive and want to get away from them. This is just how I feel. I can't really help it.

Next time we went to trivia (they invited me) but there were too many people so they said, 'we'll split into two groups. So-and-so knows all the answers, we'll put him in a group on his own.' Then they kept saying, 'Who wants to be with so-and-so?' And I got the feeling they wanted me to say 'I do!' But after the first time and all the intense questioning, I really, really did not want to be alone with him. If he started asking me questions again I knew I would feel uncomfortable again so I stayed where I was. So another woman reluctantly got up and said, 'I will be with so-and-so.'

In the future, though, I may not be able to avoid him, so what can I do? How can I gently dissuade him from interrogating me, without hurting him or making the rest of the group think I'm stuck up?

Answer 1

I will answer from the point of the person who interrogate and try to explain such behaviour before I advise how to deal with such people.

"So-and-So" probably know all answers to trivia because he like to know a lot. They read your profile before meeting you to know if there is something you can talk about rather than asking "what can we talk about". It saves time. They forced themselves of you because they, probably, read that you write and assumed that you may have interesting stories to tell.

How to deal with such people. Saying

I didn't expect the Spanish Inquisition

Is ok. So is

I don't like when people ask me so many questions without talking about themselves

They shouldn't be offended. I understand that I have more than average amount of question. You can say

Tell you what. Every question you ask me you need to answer first. And then I will see if I like the answer.

Just general remark that you are taken off by so many question will work.

Answer 2

Whilst your situation needs some refining, a very simple technique that will work regardless of your gender, the situation in the group or any other variable I can think is to simply say the following if/when he corners you next:

This conversation/interrogation is making me uncomfortable

The purpose of the bold is that you want to say that part louder. You do not want to yell it, but you want to project that part a bit more.

One answer he might have is why/what am I doing. And I would follow this why question by ignoring it an moving back to the group.

The purpose of this is simple. There is no answer he can give to this line, you will have the rest of the groups attention drawn to you and there is no further play from him.

As a line it is good to walk too, because anyone else in the group that he has done this to, even if they weren't as upfront as you have been with respect you for what you did and feel sympathy for it happening.

The one (unintended?) effect of this sort of approach is it risks exiling him. It is a solid power play within a group, and should cement you in there nicely, though it will embarrass and possibly exclude him. Again this might be useful to you, or it might not.