One of the most important aspects of dating is to have a positive outlook on things. A woman can sense instantly if you are going to be a negative and draining person to be around, and she'll go to great lengths to avoid you if you're this type of person.
Regardless of what's happened to you in your life, you CAN develop the habit of having what I call "positive expectancy". What that means it that you expect things to turn out well for you. When you meet a woman, you assume that she's going to like you, because.... who wouldn't? When you are going out with a woman, you already know that she's going to have a great time, because hey... she's out with YOU tonight.
It's important to always assume the best about people. And the funny thing is, if you see the best in people, they will tend to demonstrate the best kind of behavior when they are around you.
Now for me personally, this was a huge challenge to meet. I didn't realize it at the time, but I had dated so many women, and had so many relationship failures, that I would go out on dates, but have a negative outlook on things. I would say things to myself like, "Well, I might as well get her in bed tonight, because this probably isn't going to last anyway. I mean, look at how she was 10 minutes late. She doesn't even respect my time... and so forth." I realize that might sound a little extreme, but this was where I was at in my life. I had been burned by so many women, that I became jaded.