There are more causes for the current loathsome state of the dating world than can be counted on the hands and feet of everyone involved in the endeavor combined. But regardless of the causes, the trick is to find a method that has a prayer of addressing most of the issues.
Put into the most basic terms and evading anthropological analysis that just gets too complicated, Jewish dating is just not fun. The solution to this problem is, of course, to make it fun.
You don’t do this by planning ever more original amazing events or thinking up fantastic ideas that will blow her away and make her love you. Forget about that. To make a date fun, it’s important to understand the principles of attraction in general between people.
Attraction, speaking in neutral terms, is when two people want to hang out with each other for whatever reason. It’s based on a power differential. Between two men or two women, assuming they have enough in common with which to build a conversation, company is generally speaking enjoyed when the two parties are on the same power level in comparison to each other. Nobody feels led, nobody feels like they’re following, and the conversation flows. The guys become buddies, and the girls become friends. All well and good.
A date is a setup that attempts to build a very specific type of attraction, that of a more intimate nature. Unlike a friendly encounter, it is not driven forward by power equality, or a power differential of zero. It is in fact driven forward by a power imbalance. Going into a date attempting to level out the playing field by finding out what you have in common will usually fail. The man must lead, and the lady must follow in order for it to succeed.
Leading a conversation does not mean simply asking questions. It means inspiring the other to put in effort to the conversation. Take your average job interview. The power differential there is quite obvious. The interviewer has most of the power and the interviewee has very little. The interviewer has an easy time “attracting” the interviewee so to speak, in that the interviewee has been anxiously waiting for the interview, he’s nervous, and he very much wants the interviewer to be impressed. He is constantly inspired to put effort into what he is saying, and wants the interviewer to be “attracted” to him in turn, enough to want to give him the job.
So the interviewer’s job is easy. The attraction is already there. For a date, it isn’t as simple. Two people who don’t know each other don’t want to a priori invest effort in their conversation. They’re too skeptical to do so at the beginning. But once the initial effort is invested, attraction starts, and the rest becomes easy and fun.
A tiny example: A common question on dates, in Israel at least, is “Why did you move to Israel?” This question does not inspire the other to make an effort. It can be dodged and she can say, “I’m Zionistic” or something that doesn’t have any emotional depth. But if asked in a more powerful way, it can lead somewhere.
“I want to know what was going through your mind the moment you decided you’re moving to Israel. Tell me the story of when you finally decided that that’s it. You’re moving.”
At first she won’t want to answer. It’s a threatening question. It’s actually a demand. There’s no interrogative. Getting her to answer will require some guts, patience, and tact. She may at first say she doesn’t remember, or “I don’t know.” That means she’s thinking. Stay calm, tell her not to worry, you are very interested in the details. Give her eye contact, lean back, say nothing. She’ll want to break the silence by answering. Once she does, she’ll smile, and you’ll have a guaranteed second date. Then, by all means, find out what you have in common. To see if it could work.