Mishpacha receives many compelling letters every week, but not all of them make it into the allotted spots on the page. In one of those unpublished letters addressed to the magazine, Ira Buckman of Teaneck, New Jersey, writes that having recently made a simple, straightforward, and sincere request for forgiveness from someone he had offended led him to reflect on the rote requests for mechilah that friends, acquaintances, and relatives often make of each other at this time of the year. In the boilerplate version of “If there’s anything I’ve done this year to offend you, please be mochel me,” one rarely senses any real reflection, let alone remorse, behind those words. And so, predictably, the request begets only the equally formulaic response: “Of course. Are you mochel me?”

For his part, Mr. Buckman wrote, “Whenever a person lays the rote question on me, I respond, ‘I don’t know — what have you done to offend me?’ Invariably the person freezes. Sometimes he replies, ‘I don’t know — I haven’t really thought about it,’ to which I reply, ‘Well, you think about it and then let me know.’ On the first night of Rosh Hashanah I always make a verbal declaration granting mechilah to anyone who actually did offend me so that no one will be denied inscription in the Book of Life on my account.”

For me, the letter didn’t just provoke thought — it stirred a memory of a good friend, sorely missed. Rabbi Dovid Schwartz a”h, who was taken from us a year and a half ago, was a thinker who’d sometimes commit his thoughts to writing. Invariably, these were literary helpings born of a lively intellect, seasoned with zesty, authentic Yiddishe feeling and a dollop of bracing honesty.

IN AN ESSAY HE ONCE SHARED WITH ME about what he called “adult mechilah,” Reb Dovid wrote that he’d “always considered the most daunting vidui of Yom Hakadosh to be that of ‘For the sin of merely verbal confession.’ It is terrible to sin. Not bothering to do teshuvah for sins is even worse — but there is something morally monstrous about abusing teshuvah to the point where the teshuvah itself becomes a sin…. How many of the vidui’im that we repeat incessantly at this time of the year act as grease fires instead of fire extinguishers?”

Then, turning his attention to asking forgiveness of one’s fellow, Reb Dovid noted that already centuries ago, the Shelah Hakadosh had written of how people circulate throughout their shul for a few minutes before Kol Nidrei, asking mechilah — but only from their friends and loved ones. In the section entitled “Rosh Hashanah — Torah Ohr,” he described the scene: “ ‘Truth and peace would converge’ and they grant one another forgiveness, where none was needed… whereas those who hate one another remain firmly rooted in their places, never approaching one another, convinced that it is the duty of the other party to make the first move…”

“At least,” my friend noted, “in the era of the Shelah Hakadosh, those requesting mechilah knew whom to approach and whom to avoid. Since then things have gotten progressively worse…. When celebrities commit indiscretions, societal outrage is swift and furious. Then, when the inevitable, coerced apologies at the press conference follow, they are generally prefaced with the off-putting equivocation of ‘If I’ve offended anyone,’ as if to say, ‘What I said or did wasn’t offensive at all. Your hang-ups, insecurities, and hypersensitivities have caused this mess.’

“Through cultural osmosis, this attitude has made inroads into frum life, distorting a time-honored minhag sanctioned by the poskim into something that might be laughable for its childishness were it not so offensive. I speak of the perfunctory ‘If I did anything wrong to you, please be mochel me’ singsong repeated endlessly during Elul and on Erev Yom Hakadosh. When I am on the receiving end of such ‘apologies,’ here’s what runs through my mind: ‘Really? Really now? You’ve had all of Elul and nine of the Aseres Yemei Teshuvah to recall, audit, introspect, and reflect and you’re not even sure if you did anything wrong?’ ”

Reb Dovid observed that recognizing we have hurt someone and admitting as much to that person takes a high level of self-awareness, maturity, and courage, but that there’s yet another dynamic at work that has made apologizing properly a lost art. “Interpersonal sins are rarely clean-cut and one-sided, and as the truth of who started what, and when, grows hazier due to the ever-deepening spiral of reciprocal antagonism, we tend to rationalize our own misdeeds and to shift blame for ‘the whole mess’ to those we’ve offended. The resulting ambivalence and rationalization often yield an awkwardly phrased apology in which we hedge, partially deny or, worst of all, vent our grievances even as we apologize, which only deepens the hurt of the original offense. Rarely, if ever, are the clarity and ardor of the apology commensurate with the authenticity and passion of the actual insult for which we’re expressing contrition.”

“But teshuvah is not a game,” Reb Dovid concluded. “It is a deadly serious business that our very eternities, lives, and fortunes depend upon. In an ideal world, we would choose to do what is good, righteous, courageous, and mature, apologizing sincerely and unequivocally to one another face-to-face. But in the meantime, take the way out that’s the lesser of two evils compared to the immature way out. Just say Tefillas Zakah.”

Originally featured in Mishpacha, Issue 776. Eytan Kobre may be contacted directly at kobre@mishpacha.com