You should definitely give the guy a shot. I mean, what’s the best that can happen? 😉
Speaking from personal experience, I know what it’s like to date someone while being unemployed. It’s isn’t easy for men, especially if we find someone we’re really interested in. But if you really want to be helpful, continue to be an asset to him rather than an expense. Men are more than willing to enter a relationship with a woman who adds ridiculous amounts of value to their life.
Hope this helps.