These are all sensativities, and we cant decide them for someone else.
If a yeshiva boy would get thrown out of yeshiva for going bowling, or to a pool hall, why is it acceptable to bring a girl he is planning on building a bnb with, ok?
In Rav Folks book on engagement it is not proper to compliment one another, so why do u think it is acceptable on a date?
These are just comments, but again I cannot say rules for someone else