Most of us are good at behaving in a controlled situation. People are ready for the regular stuff on a date. The trick is to see them when something unexpected happens, like cleaning up instead of relying on the hotel staff (see above). How to shake things up (espically without looking bad) is not easy?
I knew an older gentleman who had a friend (ben brit) seriously dating an Aina Yehudia (about 65 years ago). The man who was dating said that the girl’s family were not at all against him for his religion. To which, my older friend said that the next time he is in the young girl’s parent’s house to drop a drinking glass and pretend it was an accident. Well, he did, and all kinds of words came out. That ended that.