Ironically, just hours before Lag Ba’Omer, the day we commemorate the students of Rabbi Akiva dying because they failed to show proper respect for one another, I experienced one of the most disturbing conversations I’ve had in over 25 years as a matchmaker.
I had never met “Moshe.” Someone had suggested him to a woman I know, and even though it was not my idea, I was asked to coordinate the logistics of the first date and follow up afterward to hear how it went.
Even during my initial conversation with him the week before, I felt uneasy. There were red flags in the way he spoke, but I tried to give him the benefit of the doubt. Maybe he was having a bad day. Maybe I misunderstood his tone. Maybe he simply lacked phone etiquette.
But this week’s phone call left me stunned.
After the first date, Moshe told me he was hesitant to continue because the woman was in her 30s (as was he) and he wanted a large family. Let’s put aside for now that Hashem will decide how many children someone will have. And never mind that medical research increasingly shows that men (not women) over age 35 carry greater risks for children with higher rates of certain developmental, mental, and physical health conditions, including stillborn deaths, schizophrenia, and autism.
What shocked me was what Moshe told me next.
He admitted that the date itself had gone very well. The conversation flowed naturally, and it was obvious that both sides were enjoying themselves. Yet throughout the date, he said, a voice in the back of his mind kept reminding him that she was “old.”
Then, almost proudly, he explained his strategy.
Because he considered himself such a thoughtful person, truly a tzaddik in our generation, he decided that if he ultimately chose not to continue dating her because of her age, he wanted to spare her the pain of rejection. So toward the end of the date, he intentionally acted rude and dismissive toward her. He mocked her opinions, laughed at serious things she shared, and spoke disrespectfully – all so that she would not want him.
This, in his mind, was kindness.
And, he told me, if he later decided he did want a second date, he assumed she would be nice enough to overlook his behavior and give him another chance.
I was almost speechless.
I told him that I didn’t care how many hours a day he learned Torah or how much of a Torah scholar he believed himself to be; if this was how he treated another human being, then he had failed to internalize the Torah he was learning. With his sheer insensitivity toward another person, his behavior violated one of the Torah’s most fundamental obligations: loving and respecting a fellow Jew.
His response?
“You must be a feminist.”
And then he hung up on me.
No apology. No sense of wrong-doing. No self-reflection. And no acknowledgment that this woman had invested time, energy, emotional preparation, travel, and vulnerability into the date. In his mind, the entire experience revolved around him, and his belief in himself as a righteous and considerate person.
I realized after the call that I see what is at the root of his behavior manifesting frequently and in a variety of ways in the shidduch arena. There is strong psychological research about the dating behavior that appears on the surface as pickiness, disinterest, lack of responsiveness, or rudeness, but is often something deeper: relationship self-sabotage.
Studies on relationship behavior show that people sometimes unconsciously undermine promising dating opportunities due to fear: fear of rejection, fear of vulnerability, fear of losing control, or even fear that something meaningful might actually develop. Rather than risk emotional exposure, some people preemptively damage the connection themselves. They disengage, criticize, mock, initiate conflict, reject, withdraw, or create tension before genuine closeness has a chance to form.
While people may demonstrate this behavior in other relationships, shidduch dates particularly create the perfect environment for these defenses to emerge. The uncertainty and vulnerability involved can trigger powerful emotional reactions.
Attachment styles often play a major role. Individuals with avoidant attachment tendencies may pull away precisely when things are going well or find reasons not to accept a first date altogether, while individuals with axiety attachment may overanalyze interactions or create unnecessary tension. In both cases, the behavior functions as emotional self-protection, even though it ultimately prevents connection. People can address these attachment issues and learn how to properly develop relationships.
The same dynamic that can be put into action after the dating has begun can also appear even before a first date happens. Sometimes people repeatedly reject objectively reasonable suggestions, dismiss potential matches over minor details, or convince themselves not to pursue opportunities at all. On the surface, it may look like standards or compatibility concerns. But psychologically, it can sometimes reflect avoidance: if you never give something a real chance, you never have to risk disappointment, vulnerability, or rejection.
When there is a consistent pattern of ending things prematurely, sabotaging dates, or refusing to explore healthy opportunities, the issue usually is not the other person. It is what the dating experience itself is triggering internally.
And that brings us back to the deeper message of Lag Ba’Omer.
Rav Avigdor Miller explains that Rabbi Akiva’s students were not lacking in Torah scholarship. They were genuine Bnei Torah – brilliant, accomplished, and devoted to learning. Their failing was that they did not invest enough effort into refining their character alongside their Torah growth.
Good middos are not automatic.
A person can accumulate knowledge and still fail at empathy. A person can speak words of Torah and still deeply hurt another human being. Rav Miller explains that with every page of Gemara a person learns, there must also be ongoing avoda on character refinement, sensitivity, humility, and respect for others.
Because Torah that does not transform how we treat people has missed its purpose.
We should all be striving every day to refine our middos. But sometimes, working on ourselves requires more than mussar shmuessen or dating advice alone.
When someone repeatedly sabotages relationships, pushes away healthy opportunities, or constantly finds reasons to reject objectively reasonable suggestions, it may point to something deeper that needs attention. Even the best shadchanim and dating coaches cannot fix patterns rooted in fear, insecurity, avoidance, or unresolved emotional triggers.
Sometimes, a few sessions with a skilled therapist can help a person identify the underlying issues driving these behaviors, understand what dating is triggering internally, and develop healthier ways of relating to others. That process is not a weakness. It is avodas hamiddos in its deepest form.
Building a healthy marriage is not just about finding the right person. It is also about becoming the kind of person capable of creating a life-lasting healthy relationship.
Give yourself a real chance.