1) It really depends on the situation, I can't give you a general rule here on when to flirt with compliments and when not, you have to try that out in field and if it works it does, if it doesn't it doesn't, you calibrate that by time. But I think you'll be alright, that makeup thing is very good.
2)I don't wanna kill your dreams, but after 3 months, I doubt that she is into you, othervise, she would made the move on you. Call her and aks her, where the things with you two are right now, does she wants to go out with you or not, I know it sounds risky, but I think, that after 3 months of waiting, you deserve her honest immediate yes/no answer, that way you know exactly where are you with her and you put an extra pressure at her, when you make her make immediate decission so she needs to react properly fast.
That's MY theory might be right, might be wrong
