Some of you may not like what I am about to say, but it needs to be said. It’s often more challenging to offer honest guidance that someone truly needs than to simply say the things that will make you popular. But my ultimate goal always was and always will be – to help singles get to the chuppah. And sometimes, that means having the courage to speak uncomfortable truths.
There’s been an interesting trend in how the community approaches supporting singles. We’ve moved toward what we might call “empowerment” – encouraging singles to embrace being particular about their choices, framing pickiness as a sign of confidence. While these messages come from a place of genuine care, I believe we need to recognize when this approach does more harm than good.
The Difference Between Selective and Picky in Dating
I’ve always maintained that singles should be selective about the things that matter, but not picky about the things that don’t. This distinction is crucial, and understanding it could be the key to navigating the path to finding one’s bashert.
Now, don’t get me wrong. I am all for confidence – it’s essential in dating and in life. But when we automatically label every excessive preference as “confident” or “knowing your worth,” we might be misusing the concept. What’s more concerning is that pickiness often points to one of two underlying issues: either unrealistic expectations about marriage and relationships, or deeper psychological barriers like attachment issues or commitment phobias.
Understanding the Complexity Behind Dating Decisions
Recently, I wrote a letter about the sensitivity we need to show singles, and I want to quote part of it to emphasize an important point about support versus enablement. (Click here to read the full letter)
“The truth is that singles reject shidduch suggestions for countless reasons. Some are practical; others are harder to articulate. Sometimes it’s a gut feeling. Sometimes it’s fear. Sometimes it’s unrealistic expectations or a past hurt that hasn’t fully healed. Sometimes, they don’t even understand their own hesitation.
And while it may frustrate those of us on the outside looking in, we have to remember this:
Whatever their reason, it comes from somewhere. And wherever it comes from, they are likely hurting.
We may not always understand why someone says no. Why they walk away from a relationship that seems perfect. Why they keep rejecting people who look so good ‘on paper.’
But our role—as friends, as family, as shadchanim—is not to judge. It’s not to criticize. It’s certainly not to gossip.
Our role is to treat singles with the respect, care, and love they deserve.”
This message of compassion and understanding remains crucial. However, we must also recognize that supporting doesn’t mean encouraging misguided confidence, pickiness, or unrealistic expectations. When we automatically frame every suggestion that’s rejected as “knowing your worth” or “having high standards,” we may be enabling patterns that keep singles from finding their bashert. True self-worth isn’t about holding out for perfection.
The challenge is finding that balance: supporting singles with sensitivity and understanding while not reinforcing potentially harmful patterns. Holding out for an impossible ideal is often a sign of fear, and having unrealistic expectations masquerades as confidence.
Bitachon vs Bechira (Free will)
As I was writing this article, I came across a column in the Inyan magazine written by Rabbi Avraham Y. Heschel, and I would like to quote part of it here. The question was:
“As a shadchan, I come in contact with too many people who reject any shidduch that doesn’t meet their specific, and in my opinion, narrow-minded criteria. They claim they have Bitachon that they will find exactly what they are looking for. Does Bitachon apply when a person turns down a shidduch over things that are trivial in larger scheme of life?
Here is part of his answer:
“When a shidduch is suggested, one has to have a valid reason for turning it down. Asserting that he or she has Bitcahon that something better will come up is a misuse of one of the fundamental concepts in yiddishkeit… All too often, shidduchim are turned down because of inflated egos, worry about what others will say, and emphasis on the wrong things. That is not Bitcahon; it is using Bechira, free will, to make bad choices.“
The Real Priorities: What Matters in Dating
Being selective about things that truly matter:
– Core values and beliefs that shape your life and future together
– Basic attraction that can grow into something deeper
– Compatible life goals and shared vision for building a family
– Essential character traits that reflect genuine good middos
– Shared fundamental beliefs about life, family, and relationships
Being too rigid about things that don’t matter:
– Exact height requirements that eliminate potential matches
– In-town or out-of-town
– Specific seminary or yeshiva
– Social status
– Superficial preferences that don’t affect marital harmony
Self-Reflection Questions for Dating Success
Ask yourself honestly:
– Am I giving potential matches a fair chance before dismissing them?
– Are my “must-haves” truly essential for a happy marriage?
– Do my standards reflect my values or my fears?
– Have I turned down people without giving them a real opportunity?
– Am I protecting myself from potential connection out of fear?
Moving Forward with Honesty and Support
To the singles: You absolutely deserve someone wonderful who aligns with your core values and brings joy to your life. But don’t let the pursuit of perfection or arbitrary standards keep you from recognizing something beautiful when it comes along. Sometimes, what feels like being “selective” might actually be fear in disguise.
To those supporting singles: Let’s aim for genuine empowerment. Sometimes true friendship means having the courage to ask, “Are you rejecting potential matches because they truly don’t fit your core values, or are you protecting yourself from getting close to someone?”
Let’s create a dating culture that encourages healthy standards and honest self-reflection. We must create an environment where singles feel safe to explore their true feelings and motivations.
And here, I need to add something important: In my years of coaching singles, I’ve had individuals confide in me that they simply don’t want to date or get married – whether for now or perhaps ever – yet felt immense pressure to do so. So, while I maintain that we should never ask, “Do you really want to get married?” – the reality is more complex than we might think. The pressure to date and marry can sometimes force people into a process they’re not interested in pursuing, leading to more pain and disappointment for everyone involved.
If we truly want to help our singles, we need to have the courage to speak the truth, even when it’s uncomfortable. Whether it’s addressing unrealistic expectations in dating or acknowledging that not everyone wants to get married – our role is to create space for honesty, not to enable patterns that lead to more pain. We must ask: Is “empowerment” helping or hurting?
