Trying to date while unemployed (if that is your situation) also brings up all kinds of specific problems. The What do I say when he asks what I do, the What do I say when he asks me where I work, the What does he think of me when I tell him I’m unemployed, the Do I have enough money to offer to go Dutch at this restaurant. If just speaking to people you know about your situation can be awkward, dating is practically impossible.