Meeting Naturally

He looks at me, and I look right back at him. At the moment that our eyes meet, we both glance away blushing slightly, pretending we weren’t looking at all. Perhaps he thinks I’m cute, and perhaps I am thinking the same thing about him. This scene has taken place in various forms in any number of places, be it in the supermarket, on the train, during Kiddush at shul, or on the street. The question that pops into my head is always, “Now what?”

I have friends and know people who “met naturally” i.e. without a shadchan or person setting them up. I’m just not sure how they managed to do that. I mean, take the scenario above. Great, I noticed a frum Jewish guy around my age. Assuming he is not dating/engaged/married/otherwise taken, and assuming that there is a chance we are compatible hashkafically and in terms of personality (which of course you can never really know before you find out more about the person), then how do we get from the point of “we-are-both-looking-at-each-other-curiously” to the point of talking and then possibly to dating? Note that each of those steps is a giant impossible leap. Let’s start with the first step. There is no way that I would walk up to a random guy and approach him. Social rules say that is not accepted, and even if it was I am way too shy. Unless I could make up some sort of excuse. So that leaves the only possibility of us talking up to the possibility that he will approach me. Which he will probably never do for one of the following reasons:

1. Fear of rejection. I understand that, I would be too chicken myself. Any guy who approaches a girl he doesn’t know has got to have some guts.
2. Fear that I will think he is creepy for approaching me. Depending on what he says and how he says it, this fear might be valid and I might very well end up thinking, “Why did this random guy just randomly start talking to me?” I, however, consider myself a relatively friendly person, and if a guy came up to me and said something normal, (and not creepy, for instance, “You have nice eyes.”) then I’d like to think I would give him a chance.
3. What in the world is he supposed to say??

In theory I could think of ways he could say to me, but in my mind they never seem to play out. For example, if we are in the supermarket, he could say something like, “Do you know how much this box of cookies costs?” Firstly, this seems somewhat lame, and I would never say such a thing to a guy, and if he said that to me, then I would simply answer him with the price if I know it or that I don’t know if I don’t, and then there the conversation dies and we continue along our merry ways. To sum up, it seems that even if either one of us could conquer the fear of being rejected as a weirdo or a creep for approaching someone we don’t know for no apparent reason, then the problem is that we would simply have nothing to say to start off the conversation. Perhaps it is simply that my conversation starters need some work, but I can’t imagine how a guy is supposed to approach me.

If by some miracle we were able to start chatting, and this chat was going nicely and over the course of a brief five minutes there was a mutual positive feeling towards one another, then where in the world would it go from there? He can’t ask for my number or ask me out on the spot- that would just not be OK after 5 minutes of talking. So then we depart, never to see or hear from each other again, and there you have it, the impossibility of a date happening naturally.

I just don’t understand how people meet each other “naturally.” It seems to me that the only way to meet each other is if your friends know a guy (or if you are a guy, then your friends know a girl) and introduce you. But then how did they meet that guy?

Questions for the readers: Have you ever met someone “naturally” and if so how did that go? Have you ever/would you ever walk up to someone of the opposite gender to try and start conversation? What in the world would you say?? If someone approached you, would you be creeped out? What are your thoughts on “meeting naturally”?