This story happened to the proverbial Best Boy in the yeshivah. The shiduch crisis being what it is, he was constantly being set up. Date after date, girl after girl...yet he wasn't engaged. He kept saying no, on the grounds that the girl wasn't good enough for him, wasn't worthy of being Rebbetzin Best. His parents were very worried, and called his Rosh Yeshivah to discuss the problem. His Rosh Yeshivah promised to talk to him.
The next day, The Best Boy was called into his Rosh Yeshiva's office for a talk.
RY: I'm concerned that you seem to be having a hard time in shiduchim
TBB: I know, it's so hard to find a girl who is good enough for me.
RY: I have an idea that might help. I want you to take a few months off from shiduchim. Instead, I want you to learn mussar, work on your anivus, and hopefully you will have an easier time finding a girl who is worthy of you.
So, being the excellent masmid that he was, he set up a rigorous schedule of mussar learning (bein hasedarim of course). He learned chovos halevavos and mesilas yesharim and every other kind of mussar Sefer there is. Six months later, it was a humbled boy who walked into his Rosh Yeshiva's office to say that he is ready to begin dating again.
A number of girls, and an equal number of "no's" later, the exasperated Rosh Yeshiva called The Best Boy into his office.
RY: I don't understand what's going on? I thought that after you learned all this mussar you would have an easier time finding a girl who is worthy if you! Why do you keep turning these fine girls down?
TBB: I'm having an even harder time finding a girl who is worthy of me, now that I am also the biggest anav in the yeshivah!
Obviously, this story is a joke. I like to think that it didn't happen. But, there is some truth to every joke. The truth of this joke is that there is not simply the best boy in the yeshiva. He is The. Best. Boy. And he knows it.
And therefore, I wouldn't date him.
Imagine, The Best Boy goes out with a girl, then, on the third date, he finds out that she has diabetes. WHAT? HIM, The Best Boy in the yeshivah was forced to spend a couple of evenings together with a less than perfect girl?
But that's a minor part of my reasoning. Now, I am not trying to deepen the shiduch crisis by deterring girls from going out with The Best Boy, but I don't think I would want to marry such a boy. Imagine trying to live up to it: The Wife Of The Best Boy. Ugh. I wouldn't want to deal with that.
So, to quote a friend of mine (I hope you are reading this and give yourself credit ;) "let's leave The Best Boy for other, worthier girls"
Couldn't have said it better myself. :)