יום רביעי, ט״ז תמוז תשפ״וWednesday, July 1, 2026
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Henni Halberstam is a Dating and Marriage Coach whose expert advice will help you navigate dating and relationships in order to ensure a successful marriage. You can contact her at hennihalberstam@gmail.com to schedule a phone session.
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To quote that mildly famous song, “All you need is time, time, time...” (Love. Whatever. It’s semantics.)
After an enlightening conversation about your respective Covid beliefs, you worry that you have unearthed a divide too big to bridge...
Whether you are set up by a shadchan, by a friend, or meet on your own at a singles event, take the time to do your research.
You don’t believe that they would want you, when they could look for girls who come from standard frum homes, and parents who offer more.
You have been blessed. Hashem has offered you your zivug on the first try and the parts of ourselves that fight the brachos in our lives are trying to offer you doubt when there should only be joy.
Simply standing in place or talking only to those who approach you is not enough. Instead, make eye contact, smile, and engage anyone who seems exciting.
Money can often be a source of discord in a marriage, and clear communication can help to circumvent any resentment or disagreement. This can be helped by immediately changing your view from "mine and yours" to "ours."
We are only able to control ourselves, our actions and our behaviors. We can encourage, prod, and plead, but ultimately, we are only responsible for our own conduct.
While research does not guarantee that you will connect in person, it does give your heart and mind the peace of mind to pursue someone with excitement and genuine interest.
Chemistry is certainly a vital component of a successful future with your spouse. However, a frum background and the way we date often means that chemistry does not happen in scene two or three but rather with effort and intent.
Are there girls who have everything? Are there girls that are smart, beautiful, kind, fun, and the “perfect” height? Sure!
You have not asked for sympathy, guidance or their opinion. Yet, you are not sure how you can stop the onslaught without calling more negative attention to yourself.
You are happy with the way your dates have evolved, and may even have appreciated some advice from family along the way. Somewhere, though, boundaries were lost, and solicited opinions turned into a runaway train.
I imagine that despite your best effort, you feel like you are failing to connect, and the more you worry about it, the more distant and disengaged you seem.
It would make you feel more secure before a date to go out with someone who has been vetted and approved of by your friends and family because they know her – and not because they called her high school principal from her resume.
Beyond the idealistic lens of TikTok and the like however, their marriages may be struggling, their children may live life in “time-out” chairs, and they may subsist on day-old takeout.
You are an adult and are free to make your own decisions. You also present valid points that you are welcome to share with your family as they may be saddened to hear that they have made you feel uncomfortable in your childhood home.
As more of your friends got married, I am sure that an even greater portion of the planning fell of your shoulders, and you graciously took on the task. Yet, you feel slighted and hurt at your friends’ lack of involvement now that it’s finally your turn.
Feminism, uneven expectations, and societal pressure aside, the world at large is often more comfortable with the man being older than the woman. We get you.
Building up your self-confidence, your self-love, and your self-acceptance is paramount before you go on your first date.
Listen to yourself and the emotion that you feel when you talk about her and do your best to imagine your future together. Can you picture her as a strong and loving partner?
Your best friend got married last year. She was tremendously blessed to find her zivug during such a difficult time. She likely understands this and has made peace with the small wedding she had or has planned for bigger celebrations in the future.
You don’t need to fly anywhere of course if you don’t want to. Perhaps, though, you can take a moment to reflect on your unwillingness to travel outside of your comfort zone.
Your non-existent expectations for a home do not make her basic expectations unreasonable.
It can be hard to modify the picture that you had in your head when you originally thought about your future.
While a shared background might make things easier, it doesn’t mean that it is the only way.
We all have small parts of us that don’t showcase us in the best light. Bits and pieces that when highlighted detract from our positive qualities.
You are responsible for yourself, your actions, and your reactions. Your behavior before the date, during the date, and after the date are under your control.
In shidduchim, the potential for rejection exists for everyone. Those we want to date, those we ask to date, and those we are dating, all have the opportunity to say “no” should they choose to.
You envision someone like you at this stage of your life, and your parents likely hoped for someone who shares their original goals for you.
To me, your question cannot be answered until we address your tone. Until then, this is less about your inability to see eye to eye with your parents than about your struggle to communicate properly with one another.
You believe you are stuck because no one new seems to exist in the comfortable/uncomfortable group you belong to. To remain as you are will then likely not yield new and productive results. It’s time to switch things up.
Before you allow yourself to continue on this unproductive and dangerous path, take a deep breath and refocus. Revisit the steps that got you to this point.
Perhaps girls are conditioned to get married early and to create a family and a home so they present themselves with more enthusiasm and care.
Is he helping his family financially through a difficult time and has been forced to be careful?
Take time now to heal. If that is a week, a month, or more. Be kind to yourself and take care of yourself as you process this experience.
I’m sure we can all agree that asking for a picture doesn’t stem from a deep desire to connect emotionally with someone prior to a date.
Leading however, with the notion that you are dating below your standards, or beneath your “criteria” is certainly something that your dates would feel.
Now that you are able to date again, you jumped in with enthusiasm, only to be reminded of your dissatisfying past experiences.
It can certainly be uncomfortable to mingle and connect with other guests solely to bolster and expand your shidduch reputation and reach.
You wonder how to convince girls that you are in fact a good bet, without the promise of a glitzy future.
You want to move forward, but worry that your varying views may cause friction in the future. You want to make it work, and want to know how that can be done.
Perhaps, we are getting closer to the other side and you can’t help but envision a guest-filled wedding day in the location you have always wanted.
You have taken the time to learn, to grow, and to make positive inroads in your life. You feel transformed and that makes you want to shed your past and what is represented. Yet, you are still you.
It is time to move on. What he hopes for or wants at this point is not your concern and only time will tell for him.
When we dress up for our date, we are conveying our care and interest in the outcome.
You are certainly no dummy. Clever is the name of your game. Reaching out for help is always the right thing to do.
You are two individuals, and having varied interests should not only be expected, but can be encouraged.
It is always a blessing to find someone that you connect with. But in the often-complicated world of shidduchim, your psyche has thrown a wrench at your potential future together.
Second guessing your decision when it comes to shidduchim is so difficult where clarity is the greatest gift you can ask for.
It can be hard to adjust and pivot in order to arrange a date, especially with someone who lives out of state.
Your letter was difficult to read. I hear your frustration so clearly in every word you wrote and how baffled you are by something that seems so clear to you.
Sure, she has been the bright and shiny option for so long, giving you the ability to remain in the shadows. But she never put you in the background, you allowed yourself to be placed there.
The only way to build trust is to share. This is scary because it makes us vulnerable. When we share with someone, we are hoping that they will safeguard our secrets and never use them to hurt us.
It is perfectly normal to have a specific vision for your future and can even be helpful in helping you to achieve and grow. Presumably however, you have dated people with these criteria and have not yet found the person for you.
Some daters and couples simply need more time because more often than not, both parties don’t develop a connection at the exact same rate.
The only thing that meal planning does not account for is “the toddler.” The toddler you see, always holds that one card that can’t be contested...
Your friends are seemingly dating with excitement and you don’t share their enthusiasm for a future that you are not ready for.
Your sister and her clear thrill at being engaged satisfied your friends and family while your calm demeanor worries them and now you; begging the question, “Do I feel enough?”
Unfortunately, doing the right thing doesn’t always feel good. The pain after self-sacrifice can feel extremely hurtful as you are already putting aside your own singular happiness.
The hothead gets angry because “nobody else knows how to drive!” and loses control when accidents happen (ie. a spilled drink).
To the single, it will forever place ‘single status’ blame on their shoulders alone, without any regard for the myriad of circumstances that may attribute to why someone is still not married at a certain age.
You believe you are all interchangeable at best and at worst the least shiny penny in a pocketful of change.
Often, the well-meaning suggestions offered at home by siblings and parents on whom you should be dating, and how you should be dating, only cause the single sibling pain and anxiety.
Dating can be hard and it can be disheartening. This is especially true for those that have dated for a long time.
Without the option to have been a fly on the wall during your dates, it is impossible for anyone to completely determine if it was too fast, too slow, or just enough.
While you certainly know one another now, time will only encourage the ease and comfort that you feel with one another, making your spouse someone that you appreciate spending so much time with.
You never want someone to feel compelled to marry you because a certain number of dates have passed and he feels bad, or to move toward marriage if he does not feel thrilled to be doing so.
If you have specific reasons for your anxiety write them down so that your thoughts can be clearly conveyed to those who will help you through. If it is just a general feeling of worry, write that down as well.
All those moments where you pictured the décor, the first dance, and the mile-long buffet are lost. A new dream had to be drawn that focused solely on the simcha and the union of two people ready to make a life together.
Be kind to yourself. This is hard and your pain is real. So first treat yourself with love and respect.
Living in New York will definitely allow you to access more shadchanim, more singles events, and offer you more exposure to a greater group of people.
Being smart is terrific. It is a gift from Hashem, like talent and beauty and the ability to fold bed sheets (obviously). You are smart. You know it, you want others to know it, and you want to marry someone who will mirror that intellect.
You are concerned that if she is seemingly this involved before you are even engaged, that will translate into boundaries crossed in your future with her daughter.
If Covid-19 has taught us anything – it’s that connection can still be fostered when we are not together. We can still get to know each other, build relationships, and learn from and about each other.
They take out the trash themselves, unstuff the toilet, and shlep their own luggage. These women don’t need a man, but they must not forget that they still want one.
You see the effort that your older siblings must expend in order to grow their families and you want to reject all the obligation that brings.
I will never minimize the strength and determination it takes to get dressed up, to put on a happy face, and to portray positivity and enthusiasm when you have been dating for so many years.
You are certainly lucky to have had a brother go through shidduchim before you so that you could better understand how the process works.
You are correct that there may be those who may not be interested in you because your family isn’t Instagram perfect.
While we know that they have no bearing on someone’s character, they can cause friction and uncertainty as you prepare to walk down the aisle.
Different can be exhilarating, especially if you have a tendency to be more circumspect and careful. Different suddenly allows you to enjoy the fun that spontaneity and a sense of adventure often offers.
It is heartwarming to hear that you both found a way to date that was safe with backyard benches in the place of hotel lobbies and local restaurants.
He believed that there was a myriad of choices and thus it was his prerogative to analyze every single one.
While you may struggle to talk and share, you can be a great listener. Prepare open-ended questions before the date and really listen to the answers given.
There are three categories that must be met before a couple can decide if they (with Hashem’s help) could make a happy life together.
G-d willing, next year you may look back at this precious time with your parents where you had their undivided attention for eight days.
You were happily dating when suddenly Covid-19 changed the game and forced you to prematurely think about timelines and wedding dates.
Surely, we were close. Yet, again we drove and after circling and then circling again, we found ourselves back at-nowhere.
It’s hard to go to singles events. It’s hard to smile, and nod, to introduce yourself, to offer your most charming one liner – and then turn and do it all over again.
I certainly appreciate the gift of living near your family and what a tremendous blessing it can be.
You feel like a fraud, about to be exposed for the interloper that you are, a child raised in a home filled with conflict.
My son goes home from school on a van every day with eleven other boys. Nine of them have cell phones.
Men are attracted to women with a positive attitude; to women who approach life with enthusiasm and grace, packaged in genuine self-confidence.
My heart breaks for how you must have felt sitting there struggling to keep your smile in place while your sister shared her happy news.
You also consider yourself to have depth, so it is natural to want to meet someone that approaches life with a similar lens.
Right after you stop dating someone, especially someone you have gone out with for a while, it is normal to still think about that person.
When there is someone who leans toward one group, but doesn’t tick every box, people may still encourage them to accept the label in order to expedite the dating process.
It must be incredibly frustrating to hear that you are ‘picky’ from family and friends when you are diligently trying to find your zivug.
It is always a wonderful feeling to meet someone that really seems to “get you.”
June 26, 2026 
