One of the hardest things, especially when young and dating, isn’t the ‘naivete’ so much as the energetic blind spots.
In healing work we teach, if you don’t heal it you marry it (or date it).
Does your date refuse to turn off his or her cell phone at the movies, expect others to do favors, cut in line, steal things like tableware, airline blankets, or hotel ashtrays, or insist on special treatment from the parking attendant, restaurant maitre d’, or waiter?
If you’re a woman, does he expect you to drive to his neighborhood?
Time and place might be a difficult negotiation or on their terms, especially if they sense that you’re interested in them.