Occasionally we are with someone who mistakenly hurts themselves by tripping or dropping something on their toe. When with them, we instinctively blurt out “I am so sorry.” This response is usually met with a familiar reply. “Don’t worry,” our friend says. “It is not your fault that I am clumsy!”

We colloquially say “I’m sorry” in situations that are beyond our control, but that we wish would be different. Through these words, we attempt to become closer to the sufferer by empathizing with their pain in the present moment. This beautiful gesture actually captures the entomological origins of the word “sorry” which come from the Old English root sarig, which means to feel sorrow and distress.

This time of year, during the Jewish high holy days, we are charged with the mandate of saying “I am sorry” for hurt that we have caused and therefore morally responsible for repairing. The Jewish sages say that Yom Kippur cleanses the misconduct between man and God but not between people; for interpersonal offenses, we must appease our fellow person directly.

It is not enough to feel regret and remorse for ridiculing or slandering a roommate or professor. We must approach them, face to face, and have a reconciliatory encounter.

There are moral and religious systems in which such an encounter — between the offender and offended — is not necessary for reconciliation. The Stoic, for instance, grants forgiveness as a way of distancing himself from toxic dependency that might harm his inner life. The goal is not to restore the relationship, but to achieve autonomy in order to accept what is. In Judaism, the requirement for direct contact between the person apologizing and the person offering forgiveness reflects the unique nature of the model formulated in the Talmud.

The power of a real life conversation with the people we have harmed is scary, though. It presupposes the admission of guilt, which forces us to internalize our shortcomings. At the same time, there is a serious risk of causing even more harm by bringing up a painful memory that had been buried for some time.

For all these reasons, the act of apologizing must be a premeditated gesture that is inspired by courage and hope — the idea that we can actually change ourselves and actually heal broken relationships.

The great 12th century Jewish scholar Maimonides offers us guidelines for this process: Someone who injures a colleague must verbally confess to the victim and make a commitment to change behavior. It is not enough to feel regret and remorse in our hearts; we must externalize it through speech in order for our emotions and aspirations to gain some actuality and permanence.

Rabbi Yisrael Salanter, the founder of the Mussar (character refinement) movement, was concerned that detailed apologies could potentially become counterproductive by deepening the wound, especially when the victim has long moved on or is even blissfully unaware of the misdeed. He urges us to utilize our careful discernment when offering an apology, distinguishing the need to work through specific details that require healing and those that would engender needless discomfort.

As we work on working on ourselves this time of year, I invite you to think concretely about one person who needs to hear you say “I’m sorry.” I anticipate that saying these words will be painful, but equally if not more, comforting.

Noah Cheses is associate rabbi at the Joseph Slifka Center for Jewish Life at Yale. Contact him at noah.cheses@yale.edu .