I have never gone out with a really close friend. My current gf and I have gone out several times and the first time we had known each other for a little over a month, but we have a group of friends in common. Well after we broke up it was hard to hang out with the group because of it and I really started to push her away for a while. But then I just finally got over it and we started talking and hanging out a lot again. She now probably knows me better than any of my other friends and I think it would be really hard to just be friends if we were to ever break up.

I also have 2 friends from this group who have gone out a couple times over the last 2 years and they finally broke up. The bad thing is their friendships aren't the same as they used to be and the girl is always trying to control him, which she does a pretty good job at. Its pretty messed up and being able to watch it has been enough to tell me not to date close friends.