>>5 You should spend enough time with them to know that you like them, not just at a first glance. There's no magic way to know, you have to ask them. Why on Earth does it matter if it's "awkward"? If they don't like you, you aren't going to be spending a lot more time with them, are you? It would seem counterproductive. That being said, you should spend a good deal of time with them first, so that you can both get a feeling for each other. Conversation comes naturally at that point, to start off you just have to do the basic "What do you do, where do you come from, what are your likes and dislikes", etc. You don't usually start off with a super interesting conversation, I have yet to meet someone in that circumstance.
Also remember, everyone you talk to is wondering the exact same thing as you are right now. They are, more often than not, in your boat as well. Keep this in mind.
I'm not an expert by any means, but this is what I've learned.