The sorts of experience you describe when trying to interact with people do sound reminiscent of a type of depression, and perhaps other issues. But you would need to spend time with a licensed practitioner, and be properly evaluated and diagnosed to be sure.

When social interactions become unsatisfying and you find yourself ruminating endlessly on this issue, it's definitely time to speak with a medical professional. Even if you have done so before, and come away with no diagnosis---get another opinion.