This whole thing sounds quite juvenile to me. Why not just ask her out on a date to get to know her better, rather than in a group setting with mutual friends? The chances of you two having a decent conversation and actually getting to know each other is pretty slim. I can somewhat see the appeal, since you want to be comfortable, and for her to feel comfortable as well; but this seems odd to me. I think if you had reached out to her and said, "hey, I'm interested in getting to know you, would you be down to grab a coffee/lunch/whatever with me sometime?" it might be easier to find some common ground. But maybe she is super shy and feels safer communicating within a group. Since the group date is already planned, I suggest you have fun with it, use it as an opportunity to see this person among her friends, and then ask her out on a date that is just the two of you if you are interested in pursing anything further with her.
Last edited by melancholia; 11-05-16 at 10:04 AM.
"Caring is not an advantage."