As Jo previously stated, a lot, for me; has to do with insight. Does the person I am dating know that they have issues and are they actively doing self-examination and "doing the work" to get a handle on it? Are they basic issues that many of us deal with? Are they stable on medication? Is it a major mental illness?
A few months ago, a butch on a dating site sent me an email and shared with me her history of Bipolar disorder, personality disorder and multiple psychiatric hospitalizations. I appreciated the honesty but for me, that situation was way more than I felt that I wanted to deal with. I needed to nicely state that I did not think I would be able to give her what she needed.
For a first date, I would not want to know all about someone's emotional and financial situation. At that stage, you are looking to see if you have things in common, can communicate and have chemistry. Full disclosure comes once you know that those things in place.
On a first date, fun and conversation is the primary objective. It does not cost a lot of money to have fun!
She may ask you what you do for a living. It is ok to simply state on that first date, "I am a carpenter by trade but am currently not working". If she asks for additional information, you can answer honestly to your comfort level but don't bombard her with every last detail. You can always be direct: "Is that a problem for you?". It is better to know for sure, than to need to guess.
I was scared to death when I first started dating again but it was the best thing I had done for myself in years. I also was rejected once when I first started dating and had made the first move. Luckily, I did not let it deter me and I gamely plugged along and am very happy now.
Best of luck
