It is unpreferable...., if you are going to approach make sure you are nicely dressed you don't want them to think you are trying to mug them. I actually went up to a girl and she shoved her wallet in my face with like £200 in it saying "TAKE THE MONEY!!!"....i was tempted haha jk, but nah i just told her the deal we started flirting and then i left with her number instead (so u can even come out well in a situation like that).
But yeah i have got tons of numbers off the street at like 1-4 am, i just tell them "hi there i just wanted to talk to you and look to be honest i would rather not do it at this time, but i don't like to regret anything or make excuses regardless of the situation" ...then just change topic and start your convo. So basically what you are doing is you are emphasizing with her situation and then you are paying a indirect compliment saying that despite the situation i do not want to regret this. What is there not to like?
But like i said late night approaching should be a last option, but don't let anything stop you, where there is a will there is a way.
