Here is an essay I found online:
We are all familiar with the concept of Hishtadlos; if I want to make money I have to get a job (or at least marry into money). But what really does Hishtadlos mean? The concept of Hishtadlos, is essentially, we all know Hakadosh Baruch Hu runs the world and controls everything. If that is so what do I do? How can I do Chessed or keep any of the Mitzvos if really it is all Hashem’s will? The answer is that Ain Hachi Nami the only thing I can do is make choices; do my Hishtadlos to do the right thing. So how do I know I am doing the proper Hishtadlos? What is the proper Hishtadlos?
We all know the proper Hishtadlos for some of the more basic things, like say I want to keep shabbos Kihilchasa, well first I must learn the Halachos. Second I have to tell my boss I’m not coming in on Saturdays. That’s basic Hishtadlos what about more complex issues, dating, what are my obligations towards Hishtadlos there. How do I know when that person is, or is not, for me? When should I date that person next? Where are the proper places to go on dates etc.. How pray-tell is a young man in his early twenties supposed to know the answers to these questions? The obvious answer, which every Yeshiva guy will (should) tell you, is Daas Torah, get a Rebbi and ask him. What does that mean?
The Messilas Yesharim when explaining the necessity to rely on the Torah (Chachamim) for direction gives a Mashul. A man is in a hedge maze (a maze that has very high walls so you can’t see where you are going) and there is a man standing on a bridge overlooking the maze. The man on the bridge has a great view of the maze and can provide helpful information on how to get to the end.
The man on the bridge is the Torah (Chachamim) a clear overview of what the right thing to do and the proper direction to take. The man in the maze is us, mortal human beings who have no clue where we are going, do we stop and ask the man on the bridge the means of which we are to get to the end point? Or do we brazenly say I don’t need his help I will figure it out myself, all the meanwhile taking wrong turn after wrong turn.
The Torah in the Mashul is also referring to Daas Torah, our Reebaim, great people engrossed in the study of Torah day and night, giants who eat, sleep and breathe the words of Chazal. We must take advantage of the men who have the clear view of the maze, and that is our Hishtadlos. Young adults are not expected to have a thorough, or any, understanding how to handle dating the Torah way. But, they are expected to see their shortcomings and realize that they must ask Daas Torah, they must seek people greater than them and ask their advice. I was told by one of the Mashkichim in my Yeshiva that at a Hanhalah meeting it was decided that if a Bachur did not have a Rebbi he consulted with while dating, that he was too immature to date. Now I could Hak why is that immaturity etc… but the point being that if a young adult doesn’t recognize that he does not know it all and that he needs a Rebbi to hold his hand and guide him, than it is almost inevitable that he will make grave mistakes, Because that is the mistake, a young man’s Hishtadlos is to seek guidance from Daas Torah once he does not do that he has failed to do the proper Hishtadlos!!
Baruch Hashem most young frum men, in their early 20’s, are in a Yeshiva environment, where Daas Torah is right there, and in fact I am certain that most Yeshiva Bachrim have a Rebbi they seek guidance from, for all aspects of life. But what about our future Aishes Chayil’s, where do they turn? There certainly is no system in place for a young woman to have access to a Rebbi or Rebbitzin with whom to seek guidance. And don’t tell me that women don’t need it like men do, thats silly, how could you expect a woman in her late teens to be able to know the first thing about dating? Women need guidance as well; there is no denying that. So what do we do? A Bachur has access to Yeshivas filled with Rebbaim and Daas Torah where do our Baas Yisroel’s go?
There is no system in place, for now, but we all need to accept, and recognize the need to rely on Daas Torah, not our friends, who know not much more than we do, how many times have we heard of stories of young men and women with the most mundane standards for their counterpart? Or instances where a young man or woman decided someone wasn’t for him or her because “it just didn’t feel right”, after the first date??? What exactly did you think you were going to feel on the first or second date. Now there are many different approaches to dating, and many different Rebbaim who may tell you many different answers, but your Hishtadlos is to pick ONE, it doesn’t matter who but pick a Rebbi and follow his advice because THAT is your Chiyuv Hishtadlos. Even though there is no system in place for our Baas Yisroel’s each individual Baas Yisroel should do her part in seeking out a Rebbi or Rebbitzin for guidance.
May we all be Zoche to see the end of this “Crisis” and the bringing of Mashiach Tzidkainu Bmhairah Biyamainu.



