Ask out acquaintances I have had minimal contact with or friends?
So, I am a guy from a fairly mid sized church (~400 members). With that there are plenty of singles (both men and women). And yes: I know that I do not need to limit my options to JUST my church. But, when it does come to dating inside my church, should I wait to establish a genuine friendship with someone before asking her out? Or just ask her out (maybe after a couple of in passing/in church conversations)?
Or does it really matter too much?
Bonus:
Also, I think this one is fairly obvious: "lets be friends"/"I think it is best to be friends" means anything more than friends is pretty much closed off, correct? Or am I wrong and more than friends is not necessarily closed off? I ask because I got that after closing a coffee shop with someone, we said yes to a second date initially, even had it planned, but then it was a bit confusing afterwards. Anyways.
Bonus 2:
How do you get over that one painful break up? My reactions to that person cause me quite a bit of anxiety. But, how do you get over those people who seem to stick with you?