20 year old anon here. Today I was in a downtown park and I spoke to this older girl (most like 23-25) who was on her lunch break from work at the adjacent art gallery, where she worked as a guide. She didn't seem to make much in the way of eye contact with me and she came of as a shy and geeky type, which made gaming her somewhat awkward. We talked about art and aesthetics and I talked her about my work as a musician and how I was going to be playing for an opera for an art exhibition week in another town. I complimented her shoes and told her fidgeting with the grass was pretty cute (which she admitted to being unaware of doing). By Mark Manson's terms these compliments, didn't seem to polarize her much and seemed to dial her in between neutral and non-receptive. The conversation devolved into an generic question-answer quasi-interview until she mentioned that her boyfriend was going to meet up with her after asking how longer her lunch break was. I told her I better leave before he catches me and she responded with something along the lines of "what makes you want to do that?" I then proceeded to ask her how she found her boyfriend, which she dismissed as being 'impertinent' of me to ask (it sounded more vague than impertinent to me in retrospect). She subsequently asked me why I came down to sit with her without asking and why I was asking all her questions and I told her I was genuinely curious to know her as a person. This was one occasion where I fucked up the tension building and challenging in my sets and also the closest thing I have done to what old school pickup artistry considers a neg.

What advice can you give in regards avoiding what is generally perceived as 'impertinent' questions? I asked the boyfriend question from a genuine place of curiosity and interest, but it seemed to her I was becoming too inquisitive into her personal life at that point. Also, is what I experienced (with the subsequent cynical questions she answered) a textbook example of a shit-test which I failed to a past? Also, should you always instinctively abandon or ease off an interaction upon hearing a girl has a boyfriend?