I think it depends on the kind of woman you want to date. If you are looking to date someone who also lives with family, only works part time, and has no car, you may be successful. I don't think one can really ask for qualities in a partner that they don't themselves possess. So if you are just looking to date casually and have fun, you have a real chance. You cannot provide future stability, but you can provide conversation, companionship, etc. That said, it might be a struggle finding transportation to dates and finding alone time together when you both have your families around. You both would have to depend on other people to support you and your relationship. If, on the other hand, you are looking for a woman who is financially independent with a stable career and home, that would probably be difficult. She would probably find your situation less appealing. Relationships often work best when both partners are at the same stage in life and contribute more or less equally to the relationship. You can't really do that at this point. So, I would say the answer is "it depends on what you're looking for." Of course, if you are able to start looking for a full-time job, that could really increase your chances because the financial aspects of that would help you get a car, your own place, etc. But if you have a mental health or disability issue, then perhaps you can just focus on finding companionship with a woman who is in a similar situation and will appreciate what you do have to offer.