I would try find some positive aspect and emphasize that as much as possible. A lot of my suitors dislike negativity no matter what it is. Saying: "Donald Trump is an idiot" will turn them off even if they agree. I'd have to rephrase that as "Donald Trump is kinda vile or is being very obnoxious.."
My employment status is very inconsistent and I've been in periods where I wasn't working--not a great position when trying to talk to girls. They seem to appear when you're in situations like that making conversation more difficult. I don't do much cold approaching. I get my prospects from church, school or work and there is already a working relationship involved so it's easier to keep things discreet without making the other person suspicious. Our conversations run similar to a poker game. There is an understanding we both want something from the other but we don't want to show our cards in case we are wrong. She knows my employment is not stable and I am not happy about it so that's a sensitive subject. In the same vein, I'm not bringing up love because she might not be ready to be a couple yet. Sounds like something that doesn't go anywhere, but having conversation with each other is more important than what's in the conversation.
In your case, you shouldn't be talking about yourself much if at all. All the questions should be directed at her. If she takes offensive because of your reactions, assure her that something is eating you that has nothing to do with her and try your best to spin it in a positive way that you can.