Friday, November 28, 2025

Difficult Dialogue with Dignity and Care (Jacob and Laban)

Photo from easy-peasy.ai

 A Jewish woman told me recently that her family was torn apart because of how they dealt with their differing opinions about current terrible events. Matters of life and death are certainly worth arguing about, passionately. If they can save a single human life – Palestinian or Israeli, it is more than worth it. However, many of the arguments that destroy relationships don’t advance justice, life, safety or peace. Instead, they inhibit thoughtful discussion that might otherwise achieve these very noble aims. This conundrum concerns me enough to leave my family for Shabbat to spend it with the Newtown Synagogue community to talk about difficult dialogue with dignity and care. In this blog post I share are few of the thoughts that I plan to speak about.

Care. The first element in having a challenging conversation while maintaining a relationship is to care deeply about and really see the other person, not just their opinion or argument. From care, respect flows naturally.

A stance of not knowing. One aspect of feeling affirmed in dignity, is to be understood in the way you understand yourself. For this to be work it is best that when we enter a conversation, we adopt a stance of not knowing (1). We put aside everything we think we know about what the other person is telling us and just listen deeply to exactly what they are telling us. We avoid filling in the gaps in what we are hearing with assumptions. When we ask clarifying questions, we use the exact words of the speaker. For example, if someone tells us they are reluctant to visit a place; we don’t ask if they are afraid. Instead, we ask, “What feelings or thoughts do you have about this place that make you reluctant to go there?”

Recognise the layers. Difficult conversations have three layers (2). There is the surface conversation about “what happened”. There is the emotional conversation about how we feel that is sometimes hidden. The most interesting layer is the identity conversation. This is the part where two people try to get each other to agree that they are the “good one” and the other party is the villain.  

Ensure you are ok. To manage an identity conversation, it helps not to be at war with oneself. If we are plagued by intense self-doubt, then just one harsh accusation from another person can trigger deep shame, as our inner critic finds an external ally, both giving us hell in unison. That shame might be subconscious and manifest as anger and animosity. ‘How dare you make me feel so bad’. However, if we have leaned into and thought through our dilemmas and are somewhat ok with our inner conflict, we will be less easily hurt or triggered. Being vulnerable and sharing vulnerability can be beautiful, and is quite different to being at war with oneself.    

Experience Close. On Sunday 16 November, groups of Christians, Jews and Muslims gathered in Sydney to participate in “listening circles” organised by the Abraham Conference with some assistance from Together For Humanity. We were invited to share our feelings about what has happened over the last two years. It was raw, honest, vulnerable and connecting.  Participants did not self-censor. Yet, there was no drama or hostility. Yishai Shalif (1) writes about the importance of speaking from what he calls an “experience close” perspective. If people care about each other they are interested in what the other person has experienced and it can bring them together.

Let us consider how principles of difficult dialogue play out in the story of Jacob and his uncle Laban.

Jacob was tortured by self-doubt about deceiving his dying father by impersonating his older brother Esau (3). The deception allowed Jacob to get blessings from his father that were intended for the first-born, but Jacob was not sure if he was blessed or cursed (4). Jacob had done it reluctantly, under duress – his mother insisted on it (5), “walking bent over (typical body language expressing shame) and crying” (6).  

With this inner conflict still unresolved, Jacob was an easy target of Laban. Laban had deceived Jacob into marrying his older daughter Leah, instead of her younger sister Rachel, who Jacob loved and who was promised to him (7).  When Jacob realised that he had been tricked, he complained to Laban, who then went on the offensive. Instead of acknowledging his own dishonesty, Laban attacked Jacob, stating that in “our place” (with our “superior values”), we don’t allow the younger sibling to usurp the rights of the first born (8). Laban highlighted Jacob’s own deception relating to siblings. Laban effectively turned Jacob into the villain (9). This is an easy move to use against people plagued by self-doubt.

After Jacob was chastised, his uncle Laban manipulated him into working for him, far from home, for 14 years.

One of the worst parts of the story for me is when Jacob, at his wits end after all this time, asked his father-in-law Laban for permission to go home. “Send me, and I will go to my place, and my land. (10)  Jacob told his uncle, “You know my work, that I served you.” (11)  Jacob argued that his work ethic was so strong he would succeed anywhere (12).  If Laban cared about Jacob, he would have shown interest in Jacob’s desire to be in “his place”, and also validated his assumption that he knew how hard Jacob had worked. If he had a shred of humanity, this was the time to be gracious and wish Jacob well. Instead, Laban carried on about his own business interests and how Jacob was useful to him and failed to acknowledge Jacob’s hard work and his longing to be in his rightful place.

Laban failed to care or listen with heart. This led to his family disintegrating and his daughters turning away from him (13). Regrettably, there are some people too wrapped up in themselves to sustain family ties. When interacting with them, it is important to protect oneself from harm.

Jacob, too, eventually, leans into his usurpation of his brother’s place as the first born and his deception of his father and comes to terms with himself in a dramatic struggle with an angel (14). Not long after this “encounter with the angel”, he met his brother Esau from whom he had run away from two decades earlier and they embrace (15). How Jacob achieved a reconciliation with his brother is a longer story, but the fact that he did shows that there is hope for reconciliation in families after bitter disputes.  

 

References

1)    Shalif, Y, Liviatan, I, Paran, R, (2007) “Care-full Listening and Conversations. Creating Dialogue between Members of Conflicting Multi-Cultural Groups”, Israel Ministry of Education.

2)    Stone, D., Patton, B., & Heen, S. (2023). Difficult conversations: How to discuss what matters most (Third edition, fully updated and revised). Penguin Books

3)    Genesis 27, Abarbanel commentary on Vayetze, Lamm, N, (2012), Derashot Ledorot, Maggid Books, New York, p. 148

4)    Abarbanel commentary on Vayetze,

5)    Genesis 27:6-13

6)    Midrash Rabba

7)    Genesis 29:18-25

8)    Genesis 29:26,

9)    Beis Halevi, (1990), Oliner Edition, Herczeg, p. 125

10) Genesis 30:25

11) Genesis 30:26

12) B’eer Mayim Chayim

13) Genesis 31:14-16

14) Genesis 32:25-29. Also, see commentary of Maimonides in the Guide for the Perplexed.

15) Genesis 33:4

 

Friday, November 14, 2025

Judgement and Matchmaking



“I really don’t know her,” was the reply on WhatsApp from a Rabbi in New York about a woman who was suggested as a marriage partner for one of my sons. The Rabbi was listed on the young woman’s “Shidduch” (match-making) resumé as a reference. He was replying to my message from July 2024, about setting a time to do a reference check about a potential bride. The delayed response is a funny illustration of the challenges of Modern Orthodox Jewish matchmaking.

Jewish marriage is regarded as a sacred reunion between two half souls, separated prior to birth (1). It is the fulfilment of divine design that “a man will leave his mother and father and cleave to his wife, and will become as one flesh.” (2) The tomb in which Abraham and Sarah, Isaac and Rebecca and other Jewish forebears were buried was named the “double cave” because the couples buried there were profoundly united and became part of a set (3).  Abraham cried for his beloved Sarah when she died (4).   

Ultra-Orthodox Jewish matchmaking to set up such unions has changed in the 30 -plus years since I got married. At that time, a matchmaker who knew the two families made a suggestion. The parents of the prospective young couple made a few calls to check if the young man and woman had compatible values and goals and checked out the families.

I don’t know when it changed, but we now have the “Shidduch resumé”. Men and women prepare a resumé that lists where they went to school, Yeshiva (Talmudic college post high school) or girls Torah seminary, summer jobs, some will include a short description of their qualities and those they are seeking in a partner, and a list of names of references with their phone numbers.  The parents will usually make multiple reference calls before suggesting to the young couple that they consider meeting. If they agree, they begin a series of dates.

The Shidduch process involves serious judging, but with limited information. Some references are afraid to paint their friend in a bad light. Many times, I was told, “She is not the loudest person in the room … but she is not quiet either.” I have found that it was often the little anecdotes that gave me a sense of the prospective partner’s values and character.

There is a great precedent for that. When Abraham’s servant was seeking to find a match for his master’s son Isaac, he focused on observing how helpful Rebecca was at a well. When she offered him and his camels water to drink, he decided she was a suitable wife (5).

We might feel uncomfortable making judgments; as Pirkei Avot teaches us, “Do not judge another person until you have been in their situation.” (6) However, the rules are different when there is a legitimate purpose for the judging. Choosing to spend one’s life together with another person (or advising a son or daughter about this) involves a judgement about how that person measures up against one’s own most cherished values, principles and ideals.

It sounds very unromantic but the initial part of orthodox Jewish matchmaking is similar to recruitment to fill a position in a work context. The critical question in both cases is, is it a good fit?  

In both cases there is a risk that emotion will cloud our judgement. Nobel Prize winner Daniel Kaheneman (6) writes about one way to stuff up an interview process. If you do the emotional stuff first, you might feel good about a candidate because they are similar to you, even if they lack the skills for the job. The emotional connection creates a bias. To avoid that problem, he suggests, do the boring bits first. In the Shidduch process, some young people will want to know more about the person to decide if it is a likely fit before looking at the photo and being swayed by someone’s appearance.

This might sound like a hit-or-miss approach, but if we apply Kahenman’s logic to matchmaking it is more likely to work than being guided by emotions alone.

Once the couple are deemed likely to be technically compatible, they then need to work out if they are emotionally drawn to each other.

Another element in all this is the idea of “Bashert” – that the couple are divinely destined for each other.

In the case of Isaac and Rebbecca, the match certainly seemed “bashert”. They got married and the Torah states that Isaac loved Rebecca (7).

In addition to Rebecca being a kind and sensitive woman, she was a good fit for another reason. Isaac was a reserved man who spoke little and is associated with judgement. Rebecca’s character is also associated with judgement (8). She made a snap judgment (10) about going ahead with the proposed marriage with Isaac; without hesitation, she simply said, “I will go” (11). When her husband seemed to be fooled about his eldest son’s character, because of the delicious meat Esau brought her from his hunt, Rebecca discerned the truth about both her sons (12). 

The marriage between Rebecca and Isaac was not one of constant agreement or acquiescence (13). But there was love and care, based on a sound foundation of compatibility, discovered through sound judgement.

Returning to the young woman who was the subject of the delayed WhatsApp message, at the time of my evaluation process, I was fortunate to get through to most if not all of the other eight references listed on the resumé. They provided enough information for my wife and me to suggest to my son that he should meet her. After the young people spent time dating, they made a decision by using their heads and their hearts. They are now happily married.

1)       https://www.chabad.org/parshah/article_cdo/aid/2634/jewish/The-Half-Shekel-of-Marriage.htm

2)       Genesis 2:24  

3)       Genesis 23:1

4)       The Shaloh on Chayei Sarah

5)       Genesis 24:12-20

6)       Pirkey Avot 2:4

7)       Kahneman, D., (2021) Noise, William Collins

8)       Genesis 24:67

9)       The Shaloh on Chayei Sarah

10)    Genesis 24:55

11)    Gladwell, M, (2005), Blink: The Power of Thinking Without Thinking

12)    Genesis 25:25 and commentary

13)    Genesis 27, Shlomo Riskin 

Thursday, November 6, 2025

Breaking Bread with Bishops and the Dialogue of Being and Hospitality


Humans relate better to those we categorise as friends or kin, and we can develop such connections as much – or even more- by being together than by talking. On Tuesday night, a large number of Catholic bishops and Jewish leaders had a meal together. I found it inspiring and challenging.

Bishop Greg Homeming, an older man with glasses, dressed in a very simple brown monk’s robe and sandals, spoke to us about his experiences of friendship and breaking bread with Jewish people. In his anecdotes and sincerity, he demonstrated the importance of being together.

The bishop shared his experience of having Shabbat dinner with a Jewish family. After the meal, they all began shouting at each other. His own cultural heritage is Chinese, and the lively arguing that was normal for this family of Jewish-Lithuanian culture was new and interesting for him. I have developed a friendship with this bishop, but there was another rabbi there with whom he had developed a close bond over many years. I observed them from a distance during dinner. They were in animated conversation like old friends. This was a man who walked his talk.

The bishop’s hospitality was outstanding. They organised kosher catering for us. Delicious salmon, purple and orange carrots, roast potatoes, salad, humous, fruit and two types of cake for dessert. The company was lovely, chatting about various experiences, including how bishops are appointed and visiting people in prison among other matters. As I was leaving, a bishop who had had breakfast with my son and me in July 2024 at a kosher café remembered my son’s name and asked how he was. It was an outstanding evening.

Yet, I felt a bit restless. I believe passionately in the importance of “being”, as in being present and being the best version of ourselves, as opposed to just doing important tasks. Yet, I am a product of three cultures that emphasise activity. Judaism teaches us that “action is the main thing” (1); Chabad Hasidism, under the leadership of its last Rebbe, urged relentless and urgent activism and I am a child of New York, a city that never sleep or stops hustling. I was in a room full of leaders who were responsible for the education of hundreds of thousands of children, teachers and believers and it was such an opportunity to work, yet we sat like a bunch of people without a care in the world. This was because the dialogue of being was very important for all of us. There is also something Christian (or Catholic) about the experience I had that night, that moved me even if I can’t fully articulate it.

The intersection between being, doing and hospitality plays out in the story of Abraham who was “being” inspired and elevated by a divine revelation (2). Despite the loftiness of this experience, Abraham intentionally (3) shifted his attention from the divine visitation to an opportunity to offer hospitality to passing travellers (4).  This choice is justified in the Talmud as a principle that welcoming guests is greater than receiving the divine presence, the Shechina (5).

The prioritisation of hospitality over spiritual ecstasy could be understood as prioritising doing over being. This missed the idea that for Abraham being hospitable was a deeply moving and joyful (6) experience. Abraham’s enthusiasm can be seen in the way his whole family was enlisted in feeding the travellers and the five references to speed, rushing and running in describing the preparation (7). It helps to contrast the hospitality of Abraham’s nephew Lot (8) with that of Abraham. While both men insisted that their reluctant guests join them, in Lot’s case, there was no reference to speed or any member of his family joining in (9).  

As I reflect on the hospitality, fellowship, friendship and food offered to me last night by new and old friends, I acknowledge a precious gift and I recommit to the value of being, and the practice of the dialogue of being. Not all dialogue involves words.  This is beautifully put in a psalm: “There is no talking, without their voices being heard. [Yet], in all of the earth, their message goes forth, their ‘words’ to the very edges of the world.”  (10)

1)    Ethics of the Fathers 1:17

2)    Genesis 18:1

3)    Rabbi Simcha Zisl of Kelm

4)    Genesis 18:2

5)    Talmud, Shavuot 35b.

6)    The Baal Shem Tov comment relating to Genesis 18:19

7)    Genesis 18:6-8

8)    Genesis 19:1-3

9)    Hattin, M., Vayera | Life's Concentric Circles, https://etzion.org.il/en/tanakh/torah/sefer-bereishit/parashat-vayera/vayera-lifes-concentric-circles

10) Psalm 19:4-5