... and I don't know you, so I can't read body language or between the lines of your comments. So take anything I write here with the proverbial grain of salt - hell, the whole bloody mine.

just seems like no matter how I deal with it problems will arise.

Milady, this is dating. This is letting someone into your personal space. There are going to be problems. If you don't wish to tackle them, sounds like you're not attached enough to Dave*, or even the whole idea of dating, to pursue the matter.

What do you look for in a date? If you don't know, then I would say "don't date". How can he (I'm presuming that's the direction you swing) possibly meet your criteria if you don't know what your criteria are? If I'm Dave*, I'm miserable, 'cause nothing I do really seems to work with you.

I would say, don't be pressured by your roommate's behavior into "me too". Easy enough to fall victim to that impulse, only to find out how much the results suck. Crede expertum :(. Do you and Dave share anything except mutual availability and the example of Les* and Mary*? If so, I would suggest developing those (non-alcoholic :) ) interests without emphasizing the "dating" thing. If not, tell Dave* "don't get involved with me" and look elsewhere.

I hope at least a couple of words of that make some sense, and are of any use to you.

I guess I am not actually sure if I should be dating at all.