Yom Kippur: Dating Lessons from Moshe Rabbeinu and Adolf Hitler

Moshe Rabbeinu and Adolf Hitler. Two leaders with tremendous followings who were able to greatly influence the people they led. It’s easy to contrast the two, with Hitler being so evil and Moshe Rabbeinu so righteous. They each used their gift of speech on their path to leadership, but the dichotomy between them serves as an important lesson for Yom Kippur for singles in the dating arena. 

Hitler was an eloquent, charismatic speaker who used evil and dangerous messages to attract followers, usurp power, and destroy nations. Moshe Rabbeinu had a speech impediment but used good messages to assemble followers, teach them Torah, and foster the formation of a Jewish nation united in serving Hashem. But just as Hashem allowed for the transformation of Hitler from a socially awkward, insecure, and imprisoned failure to a powerful, eloquent leader, Hashem chose not to miraculously cure Moshe Rabbeinu’s speech impediment before he embraced the mantle of leadership. We cannot understand Hashem’s actions, but we can try to learn from them.

Hashem enabled us to learn the valuable lesson of why great Torah giants have imperfections. Moshe Rabbeinu did not attract a following because of his charisma or eloquent speech. The people valued him because of what he said, not how he spoke. And while Moshe’s speech impediment was noticeable to those around him every single day, it did not prevent him from fulfilling his responsibilities in leading the Jewish nation and earning their respect and reverence.

It is humbling when people, and especially leaders, have noticeable flaws, as it checks their egos and creates a broader sense of all being equally imperfect.The Talmud notes that when the Jews were in the desert for 40 years, Hashem would dissolve the food they ate into their bodies¹, which was only a temporary basis. On a regular basis, He actually wanted our body’s natural needs to foster humility among all of us, with everyone needing to use bathrooms equally, regardless of social stature, title, or bloodline.

What does all this have to do with Yom Kippur? And what does it have to do with shidduchim?

On Yom Kippur, the tenth of Tishrei, Moshe Rabbeinu came down from Har Sinai with the second set of luchot (tables), signaling that Hashem had forgiven Bnei Yisrael. Without great charismatic eloquence, Moshe stood before the Jewish people to announce Hashem’s willingness to accept remorse and atonement from them.

This Yom Kippur, as we do our personal atonements and seek forgiveness from Hashem, it is an opportunity to remember not just the ongoing messages Moshe delivered to Bnei Yisrael but his role as the messenger. If we are supposed to look beyond the imperfections of leaders like Moshe Rabbeinu, how much more so with our peers. Just as Bnei Yisrael accepted Moshe Rabbeinu as their leader with his speech impediment, we should look beyond the superficial flaws of prospective husbands.

Yom Kippur is a time for introspection, remorse, and changing our behavior, when we should ask ourselves: Have I judged someone’s imperfections instead of their good character before declining a date? Have I turned down potential dating prospects because of superficial flaws? Or perhaps, have I invested too much time dating someone who did not have any overt imperfections, oozed charisma, and offered flirty compliments but lacked the middot I am seeking?

Most women are not dating men of such polar disparity as the tzadik Moshe Rabbeinu and the evil Adolf Hitler. But the contrast of the two teaches how careful people in the shidduch world should be, not to get easily enamored by someone’s smooth talking or easily turned off by someone’s speech impediment, or other superficial imperfection.

Yom Kippur is a time for introspection, remorse, and changing our behavior, when we should ask ourselves: Have I judged someone’s imperfections instead of their good character before declining a date? Have I turned down potential dating prospects because of superficial flaws? Or perhaps, have I invested too much time dating someone who did not have any overt imperfections, oozed charisma, and offered flirty compliments but lacked the middot I am seeking?

Rav Avraham Pam, in his writings on Parshat Chayei Sarah, notes that his mother used to say that one of the reasons that brides and grooms fast on their wedding day is to do teshuva for hurting or shaming prospective matches they turned down due to “unreasonable expectations”². Clearly and unfortunately, it is common and easy to find flaws in other people, especially prospective dates, if we want to. He’s too quiet. He’s too talkative. He’s not so smart. He’s too boring. He’s balding. He’s overweight. He doesn’t have a good voice for singing at the Shabbos table. He’s divorced. He has a stutter. He has red hair. 

In his sefer, “Living the Jewish Holidays”, Rav Moshe Eichhorn writes that the root of the Hebrew word for sin (aveira) comes from the Hebrew term for “crossing over” (avar). He explains that when one sins, they cross over from doing good to doing bad. On Yom Kippur, we work towards the reverse, putting the bad behind us and crossing over to the good. We have an opportunity to plead our case before Hashem, begging for mercy and another chance. But it must be heartfelt, authentic remorse, and with a commitment to invest in changing our ways.

We can learn from Moshe Rabbeinu that to improve our avodat Hashem and our relationships with other people, we should hold back judgment and avoid shallow assessments of others and be more discerning about what traits really matter in prospective dates. Rabbi Yissachar Frand, a Rav at Yeshivat Ner Israel of Baltimore, notes that we learn from Mishlei (14:9), “Fools find fault, but among the sincere there is forgiveness.” Each person was made “b’tzelem Elokim”, exactly how Hashem designed us, and we should be forgiving of the flaws in others, stop using shallow excuses to reject someone, and realign our expectations of others.As Yom Kippur approaches, many focus on being understanding towards our own imperfections, forgiving ourselves for past transgressions, and working to improve. It is a perfect time to commit to start having those same considerations towards others. Prepare to be an Ezer Knegdo, by being ready to support your bashert, even with his imperfections, in fulfilling whatever purpose for which you were created.

¹ Sifri 11:6; Yalkut Shimoni, Ba’ahalotecha, Remez 734.

² “Rav Pam on Chumash” by ArtScroll/Mesorah Publications