No, it wouldn't put me off going on a date with him. It's just a date - there'll be no devil looming over my shoulder, prodding me to sign a life-long contract with him. If by the end you find that he's not someone you want to pursue, the you just go your separate ways. Most people go on a date thinking they'll learn more about the person, and while that is true, most forget that you actually learn someone about yourself - what you want, what you don't want, how you handle things etc. Plus with my mental health history, I'm in no position to look down on someone who may be unemployed because of family issues and/or mental issues. As a woman, I too have found it difficult to get work. I haven't been unemployed, but trying to get out of retail these days without 300 years experience in another field is madness. I can bleat on about very real incidents that required me to have X amount of months/years to do a simple job like photocopying and filing in an office, even though I have transferable retail skills like, um, common sense and the willingness to allow them to train me no-pay. That's what I feel the job market lacks - employers who train (which basic office work needs very little of - perhaps a day at most) . That is just life from my experience; I don't know if anyone else has faced those kind of things.