December 5, 2025
“Healing Apart, Coming Together” - Rabbinic Intern Brooklyn Michalowicz
Healing Apart, Coming Together
By Rabbinic Intern Brooklyn Michalowicz
Last week, Oprah Winfrey posted a video that addresses the growing phenomenon of going “No Contact.”
It opens with clips from TikTok in which young adults explain why they've severed ties with family members.
An increasing number of people today are replacing damaged family relationships with online connection. More than 2 million TikTok users are offering each other comfort and support in limiting or cutting family contact entirely.
The screen cuts back to Oprah and her live audience, who share their stories of estrangement, asking questions to a panel of family therapists.
She frames their discussion with a staggering statistic:nearly one-third of Americans are actively estranged from a family member.
Many of us are in this painful position.
The video’s testimonies are raw and heartbreaking. One parent who went no-contact with her abusive adult son asks why parents who set boundaries are “demonized” while children who do so are “celebrated.” A young couple estranged from their siblings and parents wonders how to raise their children without aunts, uncles, and grandparents.
A woman shares that she changed every aspect of herself to fit her mother’s ideal Only to be met with rejection.
Today, generational and emotional disconnects leave people doubtful that there is room for repair. Parents tend to struggle with living up to changing and increasing expectations of the role. The demands on parents — to house, clothe, feed, educate, and therapize children versed in the vocabulary of mental health — have left many parents overwhelmed and many children misunderstood.
Siblings, on the other hand, can struggle with betrayal, differences in personality, and dysfunctional family dynamics. (1)
At times, no contact can feel like the only response.
Still, many of the guests on Oprah’s show express grief over this choice. Estrangement was the result of “a million cuts that bled them dry.”
The story of Jacob and Esau powerfully depicts the effects of estrangement.
In this week’s parashah, Vayishlach, the brothers finally reconcile after decades apart. Only by understanding this moment in the context of their fraught beginnings can we appreciate what their reunion demands of them—and what it can teach us.
After Rebecca instructs her favorite son, Jacob, to deceive his blind father and steal Esau’s blessing, she urges him to flee until his brother’s fury subsides. Rebecca imagines a temporary separation — just long enough to prevent violence.
But this “cooling-off period” lasts twenty years. Given Jacob’s 180-year (2) lifespan, that’s equivalent to a decade of no-contact for us.
In this period of estrangement, Jacob spends years laboring for his father-in-law, Lavan. Eventually, Jacob flees with his wives and children, fearful that the controlling Lavan will not let them leave. Furious, Lavan tracks them down, but instead of resorting to violence, he initiates a hard, honest conversation, and they part in peace.
I imagine Jacob had a profound realization: while fleeing imminent danger may be necessary, avoiding difficult conversations can further damage relationships.
And so, after twenty years, Jacob sends messengers to Esau’s camp in the hopes of making amends.
In all these years, Esau has grown, too; He amassed a tribe, land, an army, and made a name for himself. Here, the Torah recognizes that changing unhealthy patterns can require space rather than unsafe togetherness.
When Esau beholds Jacob for the first time in twenty years, he could have seen the face of the traitor who stole his blessing.
Instead, he simply sees his brother Jacob, aged by years of struggle.
We read:
“Jacob bowed low seven times until he was near his brother.
Esau ran to greet him.
He embraced him, fell on his neck, kissed him —
and they wept.”
What makes the brothers’ reunion powerful is not that it creates the perfect relationship or that they erase the past, but that each does something brave: Jacob steps forward with humility; Esau meets him with compassion.
Reconciliation like this requires:
1) Recognition that sometimes we need to heal apart to come back together
2) Enough humility to acknowledge when we’ve done wrong
3) The compassion to forgive, even if we can never forget
4) And the courage and imagination to forge a new kind of relationship
Experts agree that, in non-abusive relationships, going no-contact should be a last resort and should rarely be permanent.
A recent study found that those who tried to restore the relationship “regarded the healing of their family rift as the most important life experience they had ever had.”
According to the study, “[even] when they couldn’t become as close as they wanted to be with their families, they felt that having back any connection was worth their efforts.”
Many people experiencing estrangement would give anything for a reunion like this.
But I want to name something delicate here: for some of us, reconciliation is not possible right now. And may never be. Sometimes the safest, holiest decision we can make is to set a healthy boundary with the person who’s harmed us.
The Torah models that for us too, in an often overlooked detail of this family’s story: To our knowledge, once Jacob leaves home, he and his mother never speak again. Rebecca’s well-intended intervention was a major overstep as she pressured her son to do something he could never take back, while the young Jacob lacked the skills to confront her. The consequence seems to have been permanent estrangement.
Rebecca and Jacob show us that sometimes you really might not be able to be in relationship with your family.
Jacob and Esau show us that even with personality differences, family trauma, and betrayal, reconciliation may still be within reach.
For those of us in the room who have not experienced estrangement, these stories can give us compassion for those who have made this difficult choice, and perspective on how to show up for those whose grief is ongoing. And if you’ve made the difficult choice to go no contact or have been estranged by a family member whom you love, know that while the holiday season may be a sensitive time of year, you always have this community.
As we enter Shabbat, I pray that we take the time we need to heal,and reevaluate once the storm has calmed.
May we be blessed with humility, compassion, and the strength to create healthy relationships. May this be a Shabbat of brave beginnings.
1 Tina Donvito, https://www.rd.com/article/adu...
2 Post-sermon edit: This is a typo - Jacob lived to be 147 years old.
Watch our sermon above or on Youtube, listen on Apple Podcasts and Spotify, or read the transcript above.