Jeff,

First off, I have to confess that there was one time that I did not pick up the check on a failed first date. And that was a mansplaining guy who made several borderline racist comments. My guilt does not extend to jerks.

This is a thorny subject. And I tried not to editorialize too much, mostly because I have a feeling others are going to disagree with my first date/check philosophy. Personally, picking up the check ameliorates my guilt about rejecting someone. It works for me. It might not for others.

In your third date scenario, I would at least split the check or offer to pay half. Keep in mind that if someone gets to a third date and then you change your mind, it can often be because they misrepresented themselves. And some people lie. Especially with online dating, there is tons of dishonesty. And I am not talking about tiny fibs. I am talking about saying you lived somewhere you don't so you look more economically stable or failing to mention that the divorce is not finalized.

But sometimes the other person is fabulous, but not your familiar. In those situations, that ole' Catholic guilt kicks in again. Damn those nuns! ;)