I would try to concentrate on the immediate "problem" -- when asked out, I would work on going out and not worry about how in 32 dates I may have to marry the guy :-) Don't worry about anything except having a good time on a date while you're on that specific date! You can't know how it will go and whether the guy will ask you out again (or whether you want to go out again with him) or what you'll talk about or anything until you go! And, you can't "prepare" for dating, there's no pre-dating seminar/class to go to :-) It's an experience and as an experience has to be experienced to learn about it. Can't read books for experience, can't ask others, etc.

I don't know why you feel there's anything shameful about vertigo/ear problems? I had Meniere's and had that for 3-4 years myself and completely understand the depression and fear that it will never go away or be different and that you can't trust "yourself" and surroundings. I was fired from a job because I couldn't get to work one time too many and they needed someone who could should up reliably. It's an illness and for you had anxiety, etc. attached to it. No need to either discuss it in depth or fear that any one of "quality" that you want to spend time with is going to not want you as a result? If it ever comes up I'd just mention "I had medical problems" until I knew someone well enough and was comfortable with them that I could explain a bit further that I had inner ear/balance problems and that caused anxiety problems "and it was a real mess but I'm much better now." If someone "rejects" you, you really don't want them as a "friend"/love anyway do you?