Regrets When It’s Time to Say Goodbye

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There are few things more challenging and uncomfortable than sitting at the bedside of a dying person and attempting to offer some sense of comfort and calm. What do you say to someone who is about to leave this world? How do you reassure him about where he is going or try to convince her that everything is going to be alright? What do you respond when they say, “I am scared and frightened,” or, “I am not ready for this”?

We are very fortunate that Jewish tradition provides a script and a structure to help us guide someone as he is about to embark on this extraordinary journey. In the last few weeks alone, I have found myself at three bedsides reciting viduy, the deathbed confession, with individuals who, soon after, left this world. In some cases, the terminally ill patient was not conscious or awake and I simply read it on his behalf. In other circumstances, the viduy was read at the end of a heartfelt, meaningful, and powerful conversation.

Viduy provides the opportunity to get our spiritual affairs in order. I have never sat at a bedside and heard anyone regret not working longer hours or give her family instructions about physical or material endeavors. However, almost every bedside I have sat beside did include a conversation about the topic of regrets and how to make sure we don’t have any when it is time to say goodbye.

The text of viduy deals with our relationship with the Almighty and expresses our sincere apology and regret if or when we have failed Him in our lives. Viduy lets us pass from this world to the next feeling whole in our relationship with our Creator.

But just as important is the unscripted part of viduy in which we reach out to anyone with whom we may have a rift and seek reconciliation and healing. Viduy provides an opportunity to both ask for forgiveness, as well as grant it, so that we can continue on our journey without being weighed down by spiritual baggage.


As I reflected on the bedside viduy experiences I have had of late, I can’t help but think of my own mortality and the importance of not having regrets. Hearing about “what could have been” or “what didn’t have to be” is a stark reminder that we need not wait until our deathbed to get our affairs in order. There is no better time to heal, reconcile, and repair damaged relationships than the present.

Consider the following contrasting stories from this week. One headline I read says, Decades-Old Family Rift Ends with a Phone Call–American Relatives No Longer Know Why a Prewar Dispute Divided Siblings Across Continents and Decades. It is incredible to think that generations in a family didn’t speak to each other, and nobody can even remember why. If the subject of the dispute wasn’t even worth remembering, was it really worth dividing a family for generations?

Later this week, a letter emerged that Nachman had written to his parents on his wedding day to express his gratitude for all that they had done to bring him to that day. Here is the letter translated from Yiddish:

To my dear parents:

In these imminent joyous and highly spiritual moments of my life, when I’m heading to my chupa [marriage] to begin my own family, I feel a sting in my heart that I’m already leaving your warm home.

I feel an obligation to thank you for everything you did for me since I was a small child. You did not spare time, energy and money, whether it was when I needed a private tutor to learn or an eye doctor or general encouragement. Also, later on, you helped me to succeed in my Torah studies, you sent me to yeshiva to learn your values, religious and worldly, until I reached to this current lucky moment.

Even though I’m leaving your home (actually I’m not leaving, I’m bringing in an additional family member) I want to tell you that all the education and values you taught me I’ll – with G-d’s help — take along with me in my new home, and continue to plant the same education in my home and kids that G-d will grant me.

But since kids do not grasp what parents are, and how much they do for them, and only when he matures and – with G-d’s help — have their own kids, they could realize it. And unfortunately I may have caused you a lot of pain; I am asking you to please forgive me.

I’m asking you, I’m dependent on your prayers, pray for me and my bride, and I will pray for you.

I pray to G-d that Daddy and Mommy should see lots of pride and delight from me and my special bride, until the final redemption of the Messiah.

From your son who admires and thanks you and will always love you.


One family inherited a decades-old fight while another was reminded of a precious letter filled with love, communicated during the prime of their son’s life, simply because he wanted them to know how he felt.

Let’s not wait until it is too late. You don’t need to be saying viduy on your deathbed to repair relationships, communicate with those you love, or get your spiritual affairs in order. Take a lesson from Nachman Glauber and do it today.

Don’t wait until it’s too late to make your medical wishes known. The Orthodox Union, through agreement with the New York Legal Assistance Group (NYLAG), has arranged for you to register your Halachic Healthcare Proxy/“Living Will” directive FREE of charge with the U.S. Living Will Registry©.

Rabbi Efrem Goldberg is the Senior Rabbi of the Boca Raton Synagogue (BRS) in Boca Raton, Florida. He serves as Co-Chair of the Orthodox Rabbinical Board’s Va’ad Ha’Kashrus, as Director of the Rabbinical Council of America’s South Florida Regional Beis Din for Conversion, and as Posek of the Boca Raton Mikvah.

The words of this author reflect his/her own opinions and do not necessarily represent the official position of the Orthodox Union.