I had a few times I went out with a girl, but they didn't work out. One thing that went wrong was for myself I didn't have as good of an idea of what to talk about, and keep a conversation going. After a while the conversations died. I heard from a freind of mine (who doesn't have aspergers) that he was also experiencing this problem. That the first and second dates went alright but after that the conversations just died. That encouraged me to improve my conversational skills
I looked for different pieces of advice on maintaing a conversation. I found out that I should ask more deep questions like How was that, or can you tell me more about that (not just going for the basic answer). I practiced and prepared for a date with these methods, and this girl liked the conversations (she even told me herself), but it didn't work out (she did break up in a nice way) the thing that didn't make it work was that I didn't have a steady income (even a small one).
This is an example of what someone needs to do to make a relationship work.
Hat tip: Eli Massihesraelian