Dwelling over someone leads to disaster?

I don't know if dwelling can be considered the same as obsessing. But obsessions are dependent. They, of course, can be good or bad just as anything else in this world. Blah, blah, blah, it all depends on the user at hand, blah, blah, blah.

In your case, I'd still experiment. I don't know how old you are so I have no clue as to what age range of women you're after. That can very well be a factor, you know. That the women you're interacting with may have a different level of understanding than ones a couple years older or younger.

So, your outgoingness of too much care didn't work, try going with the flow.

If that doesn't work, I suggest you try this:
Find someone who can act as your best friend rather than your girlfriend. to have the most similar qualities with another is usually a surefire way of maintaining/gaining a wonderful relationship.

In my own personal experience, I had always been shy about girls/women until college came. College is a huge eye-opener. Freshmen students just stating out sort of "reset" their personality in fear of messing up with classmates and such. "Oh, I don't want them to know about this about me from my high school days. Best to act as a responsive individual than my usual perky self." And of course this leaves room for people to match each other by common ground. What do you like to do in your free/spare time? What's your favorite type of book/movie? Do you love bike riding? Wanna go eat Japanese tomorrow? Etc.

So when I was attending PSU 3 years ago, I met and got to know 3 girls. One is a South Korean international student. Very bright and determined. The other is a junkie, I suspected. I still don't know to this day, but she was fond of smoking, drinking, and partying, alot. And the third being your average athletic girl. Active, busy, energetic. I got to know really well the later two. The international student didn't really talk much and could always be found at the library.

But neither did I try to date. I wouldn't even consider it, I thought. Their personalities were so different from mine that I could find no really substantial common ground of interests to relate to them with. Think about movies you've seen, TV shows you're enjoyed. Think about those couples and how they relate to each other. They have to have something they can share to have any more reason to see each other, right? Whether it's enjoying the same sport team, understanding politics and having fun arguing about something, being actively excited about some activity they love taking part in, or something else.

Jam it back in, in the dark.