My friend doesn't think I should do it because she admits to being very traditional when it comes to these things (and I understand that as I am traditional as well). If I had little to no solid indication that he liked me, then I definitely would go with the "he needs to ask me first" route. But since the kiss et all happened, I think it's a little nonsensical to go with the tradition just because it's the tradition. If the end result is the same (- us going out) then it shouldn't matter, right?
However, she's actually had a relationship and I haven't...so what do I know?
At this point I would feel like I'm being pushy by doing it, but if a natural opportunity to ask arises then I'll definitely take it.
But I'm also confused as to why she feels I shouldn't ask him on a one-on-one date. She thinks that if I did ask him it would be less intimidating if I invited him to dinner with me plus all my friends. My other (ESFP guy) friend disagrees and thinks THAT would be intimidating and a one-on-one date is fine considering we already kissed and such.
I suppose with shy/withdrawn people, putting ourselves out there in any way that's drastically different from what we're comfortable with will make us feel like our actions are being perceived as abnormal/awkward/pushy.