Person 1,
I would recommend looking up the Shulchan Aruch, and the Rambam it is based on to see if you pshat in “schok and kalus rosh” works. Additionally, the same terminology is used by ???? ???, which is certainly not a forbidden relationship.
Lilmod,
Not talking to women more than necessary is based on the Mishna in Avos “Al tarbeh sicha im ha’isha.” But that, like many things in Avos, is understood as a midas chasidus or good religious advice. It is not brought down in halacha and is, as you said a “grey area.” Schok and Kalus Rosh are types of talking/playing/interacting that are forbidden with arayos. While there is some grey on the margins of what is considered Schok and Kalus Rosh, it seems to me that many boys dating even from good yeshivos go well over the grey line into clearly prohibited areas.
Dave & Busters is an arcade/bar/poolhall for classier clientel then a typical arcade/bar/poolhall.