Dating Was Never Meant to Look Like This: Rethinking the shidduch conversation

We keep talking about the “shidduch crisis” as if it’s some kind of a math problem but it isn't. The issue isn’t how many men or women there are. It’s how dehumanizing and shallow the dating process has become.

When people are ranked, filtered, and tossed around like products, meaningful connection becomes nearly impossible. Dating has turned into a process of scanning for red flags and searching for reasons to say no, rather than getting curious about who someone is and what might be possible between two people. Resumes have taken the place of relationship skills and this has now reshaped how people approach each other.

At the same time, we’ve moved away from environments that once made meeting easier. Summer camps, youth groups, gap year programs, volunteering, communal projects, and shared learning used to be natural places where people could meet. Familiarity could develop over time. Comfort grew through repeated exposure. Seeing someone in real life mattered.

Today, connection has largely been outsourced to matchmakers, resumes and WhatsApp lists and while those tools have their place, they don't replace community spaces and they can't. Proximity still matters. Being in the same room still matters. Seeing someone speak, move, and interact changes how people respond to them. When someone exists only on paper, it’s easy to dismiss them. Being with a real person activates something a profile never can. Interest tends to shift once there’s an actual human in the room.

Even when people do meet, many aren’t prepared for what comes next. A lot of young adults start the process without any tools for handling conflict, disappointment, repair, self-awareness or even planning a date! We put a lot of emphasis on education and achievements, but are okay leaving people clueless about their own emotions and even more clueless about how to navigate someone else’s. This shows up pretty quickly (and painfully) once dating begins. This is fixable, but only if we treat emotional skills as essential preparation for life, not something people are expected to figure out only once they start dating.

That lack of preparation feeds directly into the fear we’re seeing in dating. Dating decisions are treated like irreversible mistakes rather than part of a learning process. The pressure to choose “correctly” is so intense that many people freeze instead of moving forward. People aren’t even going on the date. They’re saying no before they’ve sat across from someone or shared a conversation. Dating stops feeling like getting to know a person and starts feeling like a test you can fail. Dating apps have only intensified this, training people to believe there’s always something better just one swipe away. Therapist Lori Gottleib describes this as an a la carte experience. When choice feels endless, people feel hesitant to show up for the choice in front of them. We don’t talk enough about how people become good partners through being in relationships, not before them.

And, it bears mentioning that some people are showing up. Constantly. They’re going on date after date, and that takes a lot of emotional and physical energy. Getting dressed, putting on makeup, rearranging schedules, making small talk with strangers, and doing it all again the next week can be exhausting. When you’ve dated a lot and still haven’t found your person, the disappointment adds up and takes a toll. Saying no can be an act of self respect and self care, not avoidance or pickiness. The point isn’t that people should say yes endlessly. It’s that fear shouldn’t be making the decision before there’s been any real chance to connect, and burnout deserves to be acknowledged too.

In response to all this uncertainty, dating culture has leaned hard on rigid rules that are not actually linked to relationship success. Things like whether someone's parents are divorced, where they went to high school, or which seminary their sister went to are being treated as decisive factors. In reality, these details tell us very little about someone’s capacity for intimacy, communication, or growth. What they do offer is a sense of control in an anxious process. But narrowing the field based on these arbitrary criteria does not lead to stronger marriages. It just leads to fewer opportunities for real connection.

Age has become one of the clearest examples of how these rules play out. Age concerns show up on both sides. Many men refuse to consider women past a certain age, often citing fertility, while many women rule out men they perceive as “too old,” sometimes based on statistics about longevity. While those trends exist on a population level, they are not guarantees for any individual relationship. We live in an era of egg freezing, fertility preservation, and evolving medical options, and family building no longer follows one fixed timeline. More importantly, age tells us very little about someone’s emotional readiness, relational capacity, or ability to build a healthy marriage. No relationship comes with certainty around health or life course. What matters far more is how two people function together and navigate life as a team..

These beliefs about age don’t stay theoretical either. They get reinforced in very practical ways, especially in how singles events are structured. Age ranges are often built on the assumption that men should date younger and women should date older, even when people are in the same stage of life. These uneven breakdowns don’t necessarily reflect preferences, but they definitely shape them. They dictate who is expected to date whom and whose age is treated as a liability. When systems constantly reinforce that men should look down in age and women should look up, they deepen the very “age anxiety” the community claims to be worried about. If we actually want to expand possibilities and support healthy matches, we need to stop designing events that bake these assumptions into the structure itself.

Unrealistic timelines also add to the panic. Not everyone gets married at 21, and not every good match comes with instant clarity or fireworks (most don’t). When the pressure grows, the options shrink and anxiety increases. Slowing things down emotionally, without dragging them out endlessly, helps people think more clearly and make more grounded decisions.

All of this pressure also shapes the way people think about choice itself. Dating advice often centers on “What do you want?” when a more useful question is “Who are you, and what can you offer a relationship?” Instead of focusing so intensely on what someone wants from a partner, it helps to also look at what each person can offer. Shifting the focus to contribution helps people think less about finding the perfect match and more about becoming a partner. Relationships work better when people think less about what they’re getting and more about how they are going to show up.

None of this works without support. Premarital counseling, therapy, and guidance from trained professionals shouldn’t be framed as a last resort or a sign of failure. Getting support earlier helps people build healthier relationships and prevents pain later. We normalize preparation in every other area of life and relationships shouldn’t be the exception.

These patterns don’t exist in a vacuum. There’s been a real cultural shift in many Modern Orthodox communities that has narrowed where and how young men and women can spend time together. There are virtually no spaces anymore that are considered appropriate for natural interaction, even when they’re communal, healthy, and values-aligned. That’s a problem. Relationships are formed and grow through shared experiences, familiarity, and being around each other in real life. What makes this especially striking is that many rabbis and educators shaping today’s norms met their own spouses in exactly these kinds of settings. Summer camp programs, communal spaces, college libraries, the “bungalow”, or everyday interactions like asking for help with schoolwork. These were normal, healthy community settings, not something “dangerous” or inappropriate.

We also need to address how leadership guidance is affecting dating in real life. When Rabbis and educators tell young men to avoid appropriate social or communal spaces where women are present, even with good intentions, it has real consequences. It reduces an already limited set of opportunities to meet and sends the message that showing up to these is somehow, “not frum,” irresponsible or not important. Encouragement matters. When respected leaders say clearly that participating in values-aligned social settings is appropriate and worthwhile, people will listen. Supporting healthy relationships and eventual marriages requires not only boundaries, but also permission to be in the kinds of spaces where connection can actually happen.

If you’re reading this and nodding along, it’s worth pausing to ask how you might be contributing to the very culture you’re frustrated by. That includes parents, matchmakers, educators, friends, and community members who pass along rigid rules, reinforce fear, over-vet matches for their kids, push people to say no quickly instead of giving something a real chance, or struggle to respect a no from someone who’s already dated a lot. Most of this isn’t malicious. It’s often well-intentioned but intention doesn’t erase impact. 

And finally, we need to stop blaming singles. This matters more than anything else. The shidduch “crisis” is not happening because people are too picky, too entitled, or not trying hard enough. Systems matter. Culture matters. Fear matters. Shame does not create marriages, support, skills, and community do.

If we want more matches and healthier marriages, we need to stop shrinking people’s worlds and start expanding them again.

None of this means we have to reinvent dating. It means we remember what we are actually trying to build. Healthy marriages don’t come from more rules, more fear, or fewer options. They come from people being allowed to connect, being prepared for real relationships, and not doing it all alone. If we want better outcomes, we need to stop putting this entirely on individuals and start building systems that make real, healthy connection possible again.

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