annual had a good way of initiating a meetup. something with friends would work very well. given that your friends are nice people, the friendly atmosphere usually opens them up. and you can never really run out of things to say bro, did you like spill your life story?? haha well even if you did, there are always random things that you notice while youre out. random observations about the world work. random jokes. random whatever, it helps for her to think youre spontaneous. use randomness in moderation though or youll just come off as a weirdo. and it sounds like the gaps between the texts is too short, maybe you could widen the gaps between texts so you dont run out of content in the first place.
"Only that escapes which was never pursued" - Oedipus the King
“Game recognize game, and you lookin’ kinda unfamiliar right now.” - Riley Freeman