List the order from hardest to least and list shy
- Good friend34%(1)45%(4)Vote50%(3)
Most Helpful Girl
Because it's neither here or there situation.
I don't have any problem asking out a total stranger, it's really easy since you just met them and there will be no confusion. If they reject you, it's fine cuz you'll never see them again.
Asking out a close friend shouldn't be that hard either. If you're close then you should already know stuff about them, what they like, what they don't, their reactions, etc. so if you "play" it right you could seduce them or flirt with them and see how it's going. Since you're close that means you see each other often and that means plenty of opportunities. You don't even have to "ask them out", in these kinda situations I think it's the best to just go for the kiss or a straight talk. I usually test the waters first and flirt the hell out of it with them, and if they do not reciprocate then well I got my answer, didn't even need to ask anything.
But acquaintance... damn, that's a hard one in my opinion. They're neither stranger or a friend and no matter how you approached them you never know how they will take it. They just might think of it like you just want to become friends, and then you're stuck in the friend-zone. Since you're acquaintances it probably means you're either work or hobby related and it is expected if them to be nice to you. so it can make an awkward mess asking them out or flirting.0