The portion of Shelach concludes with the mitzvah of attaching tzitzit to the edges of a four-cornered garment. Why? “So that you may remember Him and fulfill His commandments.”1 To illustrate this, the Talmud2 tells of a man “who was meticulous about the observance of tzitzit” and who we later discover was actually a yeshiva student, who hears about an exquisite harlot operating on a distant island who charges 400 gold coins for her services. He sent her the money and booked his slot.

We wonder what a budding Torah scholar was doing engaging in this kind of pleasure. It also seems very unlikely that this man had this kind of money to spare, so what was he doing blowing such a vast sum on this adventure?

Rather, here was an individual who was living a regular life according to his pious leanings, but who began to question whether he was missing out on worldly pleasures. So he decided to pursue what seemed to him the most extravagant adventure into the world of sin. He would go all-out to experience the height of indulgence and see what it was about.

He arrived at a palace, at the heart of which lay a chamber with seven beds, six of silver and one of gold. Each bed was higher than the next, and was reached via a ladder. At the very pinnacle lay the woman he had paid so much to visit.

Everything about the moment was designed to be overwhelming, overpowering the senses.

But just as he was disrobing, the fringes of his tzitzit slapped him in the face. As Rashi suggests, this was no coincidence. The Divine Hand was at work reminding him of who he was and what his values were. Stunned, the man slipped off the bed and slumped to the ground. The woman joined him there, confused by his sudden loss of interest. She said to him: “I swear by the life of the [Roman] emperor, that I will not let you go until you tell what fault you found in me [that made you lose interest].”

Said the man: “I swear that I have never seen a woman as beautiful as you. But, there is this unique commandment from G‑d called tzitzit …” He went on to explain the significance of the mitzvah as a reminder of our fidelity to the Almighty, Who both rewards and punishes. Despite having shelled out so much money, and despite having traversed such great distances, being confronted by the message of the tzitzit stopped him in his tracks.

He had come to experience, at least once in his life, the ultimate in physical pleasure, only to discover that there is something that has an even greater pull on a person – their relationship to G‑d! Despite the glamor and allure, even in the face of the promise of the pinnacle of human desire, he realized that there is something even more desirable – his Judaism; spiritual satisfaction.

The woman was shocked.“I shall not let you go unless you tell me your name, the name of your city, the name of your master, and the name of the yeshiva where you studied Torah.” The man wrote down this information and handed it to her.

This is perhaps the most fascinating part of the story. How did this woman know that he had a rabbi and studied Torah? Given what he had come to do that day, his behavior was hardly that of a Torah student!

Perhaps even more perplexing is his willingness to divulge his identity, given the compromising situation he put himself in. Why would he agree to provide specific information that would make it so easy for his activities to become known to his own illustrious rabbi?

This woman knew the power she had over her clients. Never before had anyone displayed that level of self-control. She realized that only someone with unique inner strength would be able to resist temptation in the manner she had just witnessed. Only a person who had been inspired by Torah would have been so transformed by the sign of the tzitzit brushing against his face.

To her it was obvious that this had to be someone instilled with Torah values, someone who had studied in a yeshiva. She didn’t ask him if he had a rabbi, but who was his rabbi. Such a person doesn’t just happen, but is the product of years of investment.

For all of the embarrassing nature of the situation, this man knew that he had prevailed and had achieved greatness. He had nothing to hide; he had acquitted himself admirably. We can only speculate about what the man expected would happen next, but it is unlikely that he foresaw what was to transpire.

Amazed by what happened, the woman decided to make some changes to her own life. She gave a third of her wealth to the crown (in exchange for permission to convert), a third she distributed to the poor, and the remainder she took with her. She made her way to the yeshiva of the great Rabbi Chiyya, the man’s teacher. “Rabbi,” she demanded, “give the order that they should make me a convert [to Judaism].”

Rebbi Chiyya sensed that something about this was unusual. “Have you perhaps set your eyes upon one of my students?” Whereupon she produced the note given to her by the man, signaling that she had witnessed a miracle that had inspired her to discover Judaism. Rebbi Chiyya understood the enormous impact this encounter had on both of them. He acquiesced to her request for conversion, and gave his approval to the marriage. “Go, acquire your prize,” he told her. “Those sheets which you laid out for him in a manner that was prohibited, now you can lay them out for him in a manner that is permitted.”

This woman thought that she had the keys to true pleasure, only to discover that there is a happiness that trumps it. The power of what she had to offer was no match to spiritual strength. All the hype around her luster evaporated when confronted with the infinite appeal of that which is holy and pure. And now that she had decided to go in search of spiritual riches herself.

In a sense, that man could be any one of us. Perhaps our story is not quite as dramatic, but the theme is not so different. We can spend enormous amounts of effort and resources in pursuit of vain satisfaction, only to come to the realization that true and lasting happiness is attained through the grandeur of the soul.