Now that the couple has navigated their way to a date - there is always the question about what to talk about. After you start with the pleasantries, asking about how your date's day was, etc. there is probably a short list of topics that you have prepared to talk about. If you haven't done this, you have just failed dating 102. For those of you who never went to college, that means the second introductory course - 101 being the first. Why it doesn't start at 100 I'm not sure.
Yes, going back to the first post, dating takes preparation. Just like most important things in life. If you take it too casually, I hope you have a very outgoing personality that can pull this off. But it also shows you are just going through the motions. How many employers would be impressed with that? You might say that it is not a job and this is not an interview and that you are looking for someone you could be yourself with. That is sort of true but only after many dates. And why is it not being yourself to prepare for something important. And if you think a marriage is something that you can just "wing it" with, then you are sorely mistaken. Maybe sometimes or even most of the time you do. But that doesn't mean that is what you should be doing. This is important. Treat it that way. You want to get close to Hashem - right (hopefully)? You think Hashem wants you to treat Him casually? I recall there being something in the Torah about not doing that.
So now that I have convince you to prepare for the date, there are a million and one things to talk about so you can choose whatever you like. There is no need to list out all the possible things to talk about. Think of some important topics. Some funny ones. Better yet, make the important ones funny. Don't think you can get through a marriage without a sense of humor.
But let me tell you what not to do - DON'T CHECK YOUR CELL PHONE FOR MESSAGES! For the very chareidi, this simply never happens because they don't have cell phones. Good for them. For those that do, this is a reminder that there was life before cell phones.
Some of my generation see this as the epitome of insensitivity. Even if you aren't interested in going out again with this person, have the decency to treat the person with reasonable respect and make it look like you’re not spitting in their face. To be fair, some of the young generation say that that's life nowadays. Everyone is so connected all the time. While that might be true, even the mainstream media have written articles about people trying to disconnect and not taking their smartphone along when they go out for the evening. While being digitally socially connected might have its place, it is most certainly NOT on a date. I suggest that you politely mention to the other party that checking your emails or Twitter feed is not appropriate on a date. If they continue to do so, I suggest you end the date immediately. Unless you are looking for someone who is inconsiderate. Just please, for the sake of Tikkun Olam, don't have any kids.
I mentioned this to a slightly older girl once recently and she replied that it is very hard for girls nowadays in the current shidduch crisis and they are told not to do anything to chase the boy away. I can see that and that is a real shame. But my reply here is that the girls have to stick together on this one and demand that the boys shape up and act like a mentsch. Letting bad behavior go unchecked will just make the situation worse for everyone. The shadchanim have to back the girls up on this and refuse to set up a boy when they get this feedback. I would even take it one step further and that the boy should be made to apologize. A public flogging for a second offense is not out of the question.