Yeah I don't think it's a good idea either. A person in the situation you describe unfortunately is also likely to have a bad self-image. There's no guarantee t

Yeah I don't think it's a good idea either. A person in the situation you describe unfortunately is also likely to have a bad self-image. There's no guarantee that a conversation with a stranger is going to go well for them. If the person they have dinner with reacts negatively in some way it may upset them a great deal and reinforce their negative self-beliefs. What they need is more money in the bank and perhaps access to counseling services. (That's the best I can come up with, at any rate.)