Ah… the first date. The halacha dictates that this date takes place in a hotel lounge over a diet coke or bottle of water. Talk should be light but discerning.
Um… light? As in what exactly? Anything conceivably “light”—as well as many things that are quite “heavy”—you tend to know already. Sometimes to the point of idiocy.
A friend of mine didn’t want to date until her older sister was engaged, so when someone redt her a fellow she insisted on knowing everything down to the color of his socks (black) before agreeing to go out. He, for his part, was jaded from being redt the wrong sort of females, so he insisted on knowing her entire biography, including the part that hadn’t happened yet, before agreeing to go out. Their first date must have been like an old reunion. As the parents shut the door behind them, he probably said something like, “I’m glad to hear you did well on that history report.”
“Yes, especially since I didn’t have much time to work on it…”
“Well you were busy with more important things.”
“True. But still, I like to do a good job on my work.”
“I hear the flu is going around Lakewood—I hope that’s not what your chavrusa caught.”
“Oh no, no way. It’s just strep—he found out this morning.”
“That’s great! So he’ll be back to learning with you tomorrow! How are you finding Yevamos?”
Etc. etc. Since they did all the dating before the dating, they were ready to get married after two dates (I kid you not), but hung out for six for the sake of propriety. (After all, what would people say? Not like it matters once you’re engaged.)
Then there are some really gauche ways to handle the first date. Here’s what one shlimeil did to a friend. He handed her a diet coke, cleared his throat, and said, “Why don’t we take turns telling what we know about each other and then we can fill in the blanks?” That did not go over well. Especially since her parents had neglected to inform her that she was going on a date until one hour before it was supposed to happen, and she wasn’t even sure what his name was.
Rov poskim agree, however, that you should either ignore those topics or rehash them while pretending you don’t know anything about them. If he provides information that contradicts what you’ve heard, things can get exceedingly interesting. Sometimes it doesn’t even have to contradict. A friend went out with a guy who she was told was accepted to Columbia. He nonchalantly admitted that he’d applied to the engineering program, which has a ridiculously high entrance rate, just to keep his parents happy, but had no intention of attending. (“Engineering? Me? Are you kidding?”)
Me, I try not to get too much information beforehand, which suits my parents, who don’t enjoy collecting it. I’d rather find out the truth from the horse’s mouth than a lot of fantasy from his neighbors who want to marry him off because “he’s such a nice boy.”
There’s a whole ‘nother sefer-worth of “halacha” about how long the date is supposed to be (one date asked me if it was OK to return me home 15 minutes before the minimum) and how long to keep them hanging before approving a second date, and on and on ad nauseum.
At this point, I just declare that hidebound regulations are “not our minhag” and get on with whatever feels right. Who has time for this nonsense?