And by 'ask out', I mean ask to go on a date with you.
Most Helpful Guy
I didn't really have much trouble except for my first few times. Other than that, it didn't matter if she was a friend or an acquaintance. I am 0 for about 900 through my life and only been on four dates- three of which just kind of happened and the fourth was set up by my aunt. I have never actually had a "yes" when i asked out women, two were strange answers : 'That's nice' in which she considered it a yes but i did not, she backed out the day of, while the second was : 'I suppose so. when she actually wasn't available (she and her boyfriend were on a 'break' but never officially ended it).
I've since decided that it was not really worth my time to pursue.
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Most Helpful Girl
Definitely a friend, because the stacks are too high and there is so much more to risk.
While with a strangers you can just walk away like nothing happened and you won't miss them if things went bad.