A girl once approached me and asked me to teach her all about dating while she stood on one foot. I answered: Be normal, זה כלל גדול in dating, and the rest is commentary.
I think a problem many daters have is they treat dating as this regimented activity with strict rules that delineate every part of the contact. This leads to miscommunication and misunderstanding, because nobody knows what the secret rules are (is there consensus on this site or any other frum site?), and because the rules are invariably ridiculous in half the contexts under which they will arise.
Every time a question comes up, you should begin by asking yourself: what would a normal person do in this situation? Almost invariably, the answer will become clear.
Let's do some examples:
1. Guy says he will take you somewhere where you are uncomfortable going (to eat, bowling, bungee jumping, etc.). What would you do if he was just your friend and wanted to go there, and you didn't want to go? What would you do if you were engaged and he wanted to do that and you didn't want to? You'd say, "I'm sorry, I'd rather not do that; it makes me feel _____". So that's what you should do here. You should do what normal people do when they are asked to go somewhere that makes them uncomfortable.
2. You walk into bagel store and guy is sitting there with his mother. What do normal people do when they walk into a bagel store and see somebody they know sitting with their mother? You go over, say hello and how do you do, and walk away.
3. Guy shows up with car seats in the back. What do normal people do when someone picks them up in a car that has car seats? You make a joke about it, and move on with life.
4. You want to break up, but are embarrassed to. What do normal people do when they want to leave a group or association with someone? They suck it up, and do it.
Being a normal person makes all the etiquette questions obvious, and makes for clear understanding between the two of you, so that you can progress to and focus on the hard part--forming a relationship and deciding if the relationship is right for you.