Dear Dr. Date,
So, I have an interesting situation here, and I would like some advice on it. The situation is this: I met a girl; she’s quite nice in the personality department, very intelligent and quite attractive. A good combination, and rare, too. I believe that she might be interested in me and I know that I am interested in her. Here is the downside of the whole matter, in several parts.
First and foremost, I have never done well at reading other people’s intentions and, therefore, have allowed myself to fall into some nasty and painful relationships in the past. Secondly, this girl might or might not be keeping me around so as to get help on things that she might not understand (I am considerably further along in my education than she, but I do not teach any of her classes, just in case you’re wondering). I have gone through being used for such purposes before and don’t like it one bit, and that has made me very wary of this and rather bitter about it, as well. Lastly, I think that there are some things in her past that might lead me to believe that she might be looking for acceptance or confirmation from me. I don’t mind the acceptance bit, but I am not the person to get self-validation from.
Maybe this isn’t a complex problem, but I am confused as to if I should pursue my interests or just give up the whole deal and look elsewhere.
— Simply Confused

If you sense that something is not right, then perhaps something isn’t right. The problem, however, does not appear to be the woman you admire. It’s you. Don’t you think you are searching too hard for a reason not to date this woman? Your confusion isn’t simple indecisiveness. You appear to be desperately grabbing for reasons why it doesn’t feel right.
Your concerns are all valid, but I think you are letting your pragmatic side dominate your thinking. There are certain areas in life where well- reasoned, rational behavior is better, such as investing in the stock market and buying a house. Dating allows — and often requires — that you behave abnormally. In an effort to rectify my dating situation, I once drafted a list of 63 requirements that all future dates would have to meet. As it happened, I did not date until after I ripped up the list.
I suspect you might be lugging around some rather cumbersome baggage from a few of your past relationships. It’s unfair to assume that any new women you meet will behave like women you’ve dated in the past. Clear your mind and give this personable, intelligent and attractive woman a chance. She sounds wonderful.