יום שני, י״ד תמוז תשפ״וMonday, June 29, 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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One of the hardest parts of dating is that people rarely arrive at the same place at the same time.
You need to let your friends and family know that you are ready to date so that they can peripherally assist you as well. You need to keep this circle tight and small.
When a guy doesn’t pick up a girl for a date, it steals some of that thoughtfulness from the date. It diminishes effort and energy. It robs the date of the romance it could have had. That’s a loss to both you and to him.
You are not missing anything. Everything has been going smoothly because it can. You don’t need conflict or disagreement. You don’t need an issue to address or a problem to fix.
Six months is definitely enough time for a man and a woman to decide if at the very least, they want to commit to one another. It is certainly enough time to see if they are compatible, if their personalities align, if they have the same life goals and values, and if they have chemistry.
You put in time and effort and forged an emotional connection. Unfortunately, he might have been right there alongside you, but he has not arrived at the same place.
Make eye contact. This feels so simplistic, but I have noticed that in the fast-paced world we live in, we are often looking beyond or around the person we are talking to.
The beauty of dating is our ability to measure if a connection can be made. So much of this is done through research and information gleaned before we even meet. But the actual date allows us to see if the match made on paper can translate to chemistry and a lasting relationship.
It is impossible to romanticize long-term learning without the financial component. The stress of not being able to cover your tuition bill, to make your car payment, or pay your rent, cannot be dismissed.
It’s time to assemble a team. Mothers have the unique ability to manage many hats and their absence must often be filled by more than one person. Find the two women in your life who you trust, and who genuinely care about your well-being.
This is very common. Sometimes you are just not in a relationship mode (especially early on) between dates and your brain naturally shifts back to your regular life (routines, work, family, etc.) when you are not with him.
The incredible part of marrying someone and becoming a new entity, however, is the ability to build on the foundation your parents have given you, but with your own flavor and your own choices.
Date her. Find out about her. (Find out about her weight-loss journey.) See if you are suited for one another. See if you connect. And then make a decision with all the information that you have.
Sure, he is not shorter than you, but you wanted someone taller. One more inch. That doesn’t seem so much to ask for.
At some point, every single boy or girl who has dated longer than a year has heard the dreaded, “Maybe you are too picky.” from someone invested in their shidduch process.
Let yourself breathe. It’s OK to mute the engagement/vort/shower/baby chats. Allow yourself to skip an engagement party when it feels like too much.
A resume allows you to offer clear, concise, and direct information to someone potentially interested in you. It allows you to control the narrative and the information direction that others take when someone suggests your name.
Allow yourself to feel disappointed that dating has not gone as you had hoped. Forcing positivity and enthusiasm doesn’t work.
I know that when we see potential, when we see beauty and possibilities, we tell ourselves that we can figure this out. We convince ourselves that we need to look beyond the logistics and the minutiae to focus on the bigger picture, and the chance for long-term happiness.
To your credit, you were not planning for this to happen. But you truly believe that this is something real and right and you have made a commitment to each other.
There are inequitable and unfair judgments made by those with sons in the dating world. For reasons never fully understood, boys have an advantage in dating.
I know you are coming from a good place. I know that you just want what your friends got. It’s not your fault that you live in an Instagram world filled with photo ops instead of memories. And I want you to have a special proposal. I really do. Just not the one you are picturing.
You know that part of forging an authentic connection is sharing, but you are scared. Because, of course, it’s scary to share.
He is not changing. This is who he has been for a long time, and will likely be for the foreseeable future. Of course, we are all capable of growth, but he is who he is, and that will not be different in three weeks or three months.
You have been given a gift. You met a girl who seems perfect for you. You like everything about her and are considering an engagement. Your friend didn’t want to marry her. This is an even greater gift! She was clearly meant for you and not for him, and that was clear to him and we hope now to you as well.
Sometimes a person who does not have the emotional maturity and mentchlichkeit we expect of them will deflect and redirect so that they don’t need to be honest and transparent.
Even if the guy you are hoping for is so outdoorsy he fillets his own fish at restaurants, he is still going to be affected by your appearance.
Green flags do not offer the same shock value as their red counterparts, but they are even more important.
After three weeks, you should be sure that you are able to communicate well and have shared values and goals. You should have formed some level of connection and have an appreciation for their character and personality.
Do you also notice those flaws? Do they bother you? If they do, why don’t you take steps to change them?
For an introvert, dating can be painful, as they struggle to overcome their innate reserved personalities.
While self-confidence is key, the ability to be humble is vital.
It is not wrong for you to look for a guy who has a solid plan for the future. It is not wrong for you to look for someone who cares deeply about doing whatever it takes to provide for his family. It is not wrong for you to look for a person who is emotionally stable and diligent. Unfortunately, we cannot predict the future.
You are certainly in command of your own decisions. And dating is hard. And exhausting. Unfortunately, you are absolutely being short-sighted and overly selective.
Use this as an opportunity to widen your circle. Share meals with new people, attend community events, and visit new places. This will allow you to meet people who are not in your direct social circle who may have new dating possibilities for you.
I appreciate your willingness to put in the work. You are happy to do the “right thing.” You just don’t know what that is anymore.
As members of Klal Yisrael, I would hope that we would all offer empathy and compassion. Telling someone NOT to feel is not our way. Discouraging someone from feeling sad or mad or hurt doesn’t work. It doesn’t erase feelings.
First, you need to believe in the system. You need to have faith in your parents and their research. You need to have confidence in their understanding of you and your wants and needs.
We don’t have to establish that you love your sister and you want to see her happy. We take this as fact. Regardless, the sadness, shame, and anger for feeling this way are eating at you.
No couple has a completely seamless dating experience. None. Sure, some daters go through this process with ease and some struggle, but regardless, there is no perfect dating journey.
A guy who immediately suggests that you change in order to meet their approval is not someone you can keep in your life.
The goal of dating is to get to know someone better, to build a relationship, to get engaged, and to iy”H get married. This should mostly be an insular experience between two people. Yet, we live in a world that loves to share and impress.
You had this upcoming year planned, and part of that included dating. Now you worry that this might not be the correct decision. Should time be factored into your hope to date and if so when would it be right?
In some way every student comes home a bit changed – hopefully improved, and ready to tackle a new and exciting time in life. Sometimes that change is more significant, more obvious to our family and friends – perhaps in the way we dress, speak, or in a newfound commitment to Torah study.
You see your date’s internal beauty and you are not bothered by a lack of the typical commercial good looks we are taught to value. But you worry that you will be influenced by the subtle judgment you expect from those that know you.
Strengthen your relationship with Hashem. Daven, connect, and bolster your emunah. Ask Hashem for what you want, ask for the strength and the wisdom to recognize what is right for you, and make sure your connection is real and sure.
You don’t need a girl who see you and sees short. You need a girl who sees you and understands that you are everything she ever hoped for.
In the beginning, perhaps you appreciated the input and research your parents offered, but now things have changed. You are less reliant on their suggestions and opinions and trust yourself to make good dating choices.
While marriage is holy and beautiful, it is also a huge responsibility. It is a parents’ duty to make sure that their child is physically, emotionally, and mentally prepared for this lifetime commitment.
I’m sure you are a wonderful guy, and clearly, you are not to blame for the uneven balance of our dating system where girls seem to be the underdogs. You want to date right, but there is a limit on the excitement you can conjure when every date feels so similar.
More likely, the shadchanim and your family and friends are making valuable suggestions that your ego refuses to consider.
We forget to look in the mirror to acknowledge our beauty and successes, and instead, open every window to let in our failures and disappointments.
If your parents are not the right resource right now, find someone who is. This can be a Rebbetzin, an aunt, a close family friend, or a therapist. It’s true that many kallahs feel nervous after getting engaged and it is possible that you are simply one of them.
We tell ourselves every day that mistakes define us and shape us and in turn they hold us back from improvement and change. But what if you ate the cake, enjoyed it, but ultimately decided that it was not in your best interest?
Perhaps, you feel closer on one date and less so on another. This is common, and patience and some encouragement can be all that we need. That being said, when we actively notice that we like someone less and less as we date, we need to recognize and take note.
It is so exciting that you have met someone that you are contemplating a future with. But with Pesach and the spotlight on minhagim and customs, you now see your differences in a new light. You worry that this will be an adjustment you might never be ready for and may be too much to take on.
Dear Dating Coach, I am not going home for Pesach. Nothing you say will convince me to change my mind. I am dating someone pretty new in the city that I am currently living in and I want to continue dating him over Pesach. My family lives quite a distance away. So, I have […]
Your inability to see past a picture, a number (both height and weight!) your impudence over color preference, and your arrogance in creating a Ken doll just for you, will leave you not only without a date, or mate, but a future based on Torah values.
You like him. You really do. You have had a great time together. You connected. Your parents did extensive research. They know he has qualities that they felt made him worthy of you. You have spent time together. Now, trust yourself. Trust the process.
There is an art to communication, where you truly listen, absorb and then discuss what you have heard. You cannot leave or walk out when you don’t like the discussion.
Take the time to self-reflect on your growth and sense of responsibility. Are you capable, emotionally stable, and grounded? Assess your ability to navigate the world around you, to stay the course during challenges, and to take care of yourself. If you feel like you have those in the bag, you are probably ready to date.
Nobody will care about his resume or yours. Nobody will gape at your age difference. And nobody will ask how you could have dated a teacher. EVERYBODY will be too busy admiring your blessed connection and your wonderful happiness.
We should care about our appearances and do what we want to make us feel good both inside and out. What this might mean to one person might be different to another.
Take a deep breath. You are doing so well. Dating someone you like, and feeling positive about your dates is huge. Everything was going nicely until your sister’s blanket statement about timelines and expectations through you off course.
You need to be fully engaged on your dates. Make eye contact, allow your body language to showcase your interest, and listen carefully to what your date is saying. Show them that you are fully present and happy to be with them.
There is no room for arrogance in dating. There will always be someone prettier, richer, smarter, and more talented than you. There will always be a girl who is more than you. If you do not see these girls, and only see those that are less than you, read this article carefully.
A dater must always have an open mind. Objectivity and humility are central to dating and there are certainly times when we can lose ourselves in the exhaustion of it all.
Reflect on the moments where he yelled or screamed. You may notice that there are even more instances than you originally noticed.
While this is not simple, it is certainly possible. While, you may see that you are less malleable, you may notice that you are wiser, and more focused on what truly matters in building a happy life.
It is inappropriate to date two girls at once. This applies to any number of dates that have passed. It’s wrong and there is no way to change that.
Sit down for a minute. Just one minute, because this is going to be hard for you to hear. Date him. Date him with intention and an open mind and heart. Focus entirely on him when you date and give him the best version of you filled with enthusiasm and positivity.
It's okay not to attend. You don’t need to give a reason. You can just say that you wish her the greatest happiness but you won’t be able to fly in. That’s it. No explanation necessary.
People look different in person, and you know… when they are not two dimensional. People look different after we talk to them, after we connect with them, and certainly after we LIKE them.
While this is someone you really like, someone you even imagined marrying, you are not comfortable in this place of indecision. You don’t want to make a mistake by dismissing the person who could potentially be your zivug, but you are also not happy to live without any form of real commitment.
We are Jews dating Jews. Regardless of your background or hashkafa, right or left, black hat or baseball cap, look for someone who believes in Da'as Torah.
It is possible that this couple is not meant for one another. It’s possible that they will be better off going their own ways and finding different matches. It’s possible that their son knows absolutely that his feelings will never change.
You feel like you are close to an engagement and understandably want and expect the support of your family and friends. Yet, they are refusing to give you their blessing and have expressed concern instead.
I am more often than not of the belief that another chance is the way to go. If the possibility even exists that this could be your match, you are looking at a lifetime of connection and happiness at best.
Dating can be easy for some. They date one boy or two, they connect, build a relationship, and soon after they create a home and a family. For others, dating becomes complicated.
The solution is to stop going home. Just kidding. That would be a terrible solution. Instead, go home and have a sentence of appreciation at the ready.
You need to take yourself into account. You need your family now, their love, and the comfort and food from home. You need to spend time with family, and you need rest. This matters too. This matters more.
Some people view dating like they would, sitting in traffic, or a in a parking lot. They believe you need to wholly focus on dating and getting married, and once you have accomplished that, you can expand and grow. So, they go to work and come home.
What I find to be most objectionable however, is your statement, People today believe, (especially wives) if I make money that means I’m equal to a man. Bless your heart.
What an uncomfortable burden to carry! You believe that you have become a responsible and well-liked adult with good character and middos. Yet, you still worry about becoming the spouse you watched in your home.
I think the reason that the guys are not able to validate your argument however, is not because they can’t agree on your delineated list of chores. I believe instead, that your fifty-fifty attitude is probably holding them back.
You family has done you a disservice in not being more transparent about the money that they earn to afford the lifestyle that they have raised you in and the effort that it takes for them to get there. Life in expensive.
Perhaps though, decide to rely on Hashem and relinquish the power you are clinging to with shaky hands. Tell your parents that you would like to discuss the option of your sister dating as well and surrender your role as gatekeeper to a greater master plan.
Take a moment to catalogue the net you have cast in shidduchim. Have you only reached out to people in your community, your state, or your exact upbringing? Consider widening the net to include a broader scale of possibilities.
I know that this will be uncomfortable for you to hear and will not offer you the satisfaction and peace of mind that you crave, but I need you to stay in your own lane. Unless you or your chosson are contributing financially to the wedding, this is not your business.
It might be prudent to explore why you have kept this secret. Sometimes we are conditioned to be ashamed, embarrassed, and diminished by those who love us best because they worry about shidduchim, or perceived judgment they imagine you will face.
Many couples in your circle will get married and build loving and successful lives together. They are the waves we can rely on. They reassure us and give us hope for ourselves.
If a kallah was writing with this question about her chosson, I believe that there would be little to no pushback. A girl is allowed to notice clothing, but a guy is not?
Sometimes we want something so much that we negate things that typically matter to us.
I agree that a six-week break so early in your dating process is complicated and perhaps even unrealistic. When your connection is still so tenuous and new, it can be hard to nurture it with six weeks dividing you.
It is true that if you date your friend’s brother and it doesn’t work, even with care and respect, it is unlikely that your friendship would be unaffected. He is her brother, her family, and as much as she loves you, there is great potential for awkwardness at the very least, and even a ruined friendship.
I appreciate your position. I really do. At the same time, the chance (even the small chance) that this could be your happily ever after means that you need to try.
Of course, you both feel torn when faced with their concerns. They are your parents and you are conditioned to agree with them. At the same time, their disagreements are not yours, and are creating painful conflict between a couple that otherwise feels just right.
If you are asking me if being happy is a bad thing, I couldn’t possibly disagree. If you are wondering if I believe in being mindful and present, then the answer is of course, ‘yes.’
A reputation is something that someone builds over time, so we can trust that this is going to give us a better understanding of their true character and behavior.
It is possible that there is something you are missing when it comes to his family, and it is equally probable that whatever has caused their disconnect will assure you of his commitment to an emotional connection and his stability.
June 26, 2026 
