After giving it some thought over the years, I really don't think it's a good idea going for dating to the circles where you will comfortable. You will most likely get friendships that way, but I am not so sure about dates. But if you actually try to go out of your circle and do something different you might stumble upon a girl who you will explain that you are new to this and that and ask her to give you some advice and help. With somewhat you are familiar with like in the situation A above, there will be far less space for conversation other than some advanced talk on the things you both like. That will be pretty much what it is: two whatever-geeks sharing what they know about something. But situation B is different, you're going out of your circle of comfort, giving up yourself to somebody and their interests in a way and that is how you will leave a very good impression. People like other people expressing genuine interest in what they do and they feel the need to respond with same interest for what you know and before you know it something wonderful may happen. It's not a thing that will happen at once, but I think that for a change you should try something like that.