יום חמישי, ז׳ אלול תשפ״וThursday, August 20, 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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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.
You need to discuss what your individual financial expectations are. Not only about what you will each be contributing as a couple, but also about what you expect your spouse to offer you in terms of gifts, vacations, and the like.
Sometimes, we need guidance and counsel. Sometimes, we can benefit greatly from advice. Yet, there are times however, when too many voices only cause chaos and pain.
Even when things are going well, we may have bruised feelings when we feel a stronger connection earlier that the person we are dating or feel ready before they do. We are all responsible for our own feelings. We get to decide on the risks we take with them.
Time to set some boundaries. This has to be done right away before you are all gathered at the Seder table.
It’s time to slow things down. Nothing has changed. Everything is still going smoothly. You still like each other. You still want to continue dating. The only addition, is that he is ready to discuss your future, and you are not – yet.
Someone is calling you to ask about this person’s character, intelligence, background, and more. They are not asking you to predict the future, to see through your crystal ball, or to decide the fate of the person they are calling you about.
The resume is your introduction, a basic understanding of you so that potential daters (and their parents) can surmise if you might be at all compatible. Instead of fighting it, use it as a wonderful tool. This will help you to not go on dates that don’t make sense for you.
Go back to the shadchan and ask if they ever use tinfoil pans versus real ones. Investigate their ongoing Shabbos purchases and detect if they have ever purchased take-out or used a plastic tablecloth.
I don’t think a cup of coffee is cheap. I don’t think a walk in the park is cheap. I don’t think a date that costs zero dollars is cheap. I do think however that your FOCUS on the cost of Java really refers to the lack of FOCUS on you.
Think of questions that are both light and deeper to get to know your date as organically as possible while still focused on the goal: to see if you are compatible.
It is frustrating to go out, have a pleasant time and then hear that the other person does not want to see you again. It is even more upsetting, when this happens multiple times with multiple guys.
Woman are looking for a man. This is more than a gender – it’s character. Women want someone they can rely on, emotionally, physically, and yes, monetarily.
If they are lucky and nothing egregious or ‘red-flaggy’ happens on that first date, they go out again hoping to ease into ‘slight unease’ on their way to ‘dating comfortably.’ This is reality.
I can’t imagine that you expect that everyone who goes on a date is immediately attracted and excited about the person they meet. I would boldly suggest that many people who go on first dates are less than thrilled about their dates’ first impression.
At the very least, take a few minutes every day to sit quietly, to intentionally relax your muscles and to release the stress and knots that have certainly taken root under your skin.
Today, daters are careful when they determine what characteristics matter to them. I hear a lot of words like, smart, outgoing, ambitious, spontaneous, and educated. These are all good words.
The only way to fix this is by changing the game. Instead of two parties, we need three.
Let me start by saying that I hope you meet in the middle. It would be wonderful if you were both on the same page in hashkafa and could ride off into the aqueduct, er, sunset.
When something is not working, when something feels unhealthy, or unproductive it’s smart to step away. Sometimes we need to remove ourselves so we can see what hasn’t been right for us.
Sit down with your parents, a dating coach, a trusted mentor, or rebbetzin. Tell them how you feel and how you DON’T feel. Be honest and forthcoming without shame.
Sure, I would not be so glib as to deny that our appearance and even size matter in shidduchim. Perhaps there is even a point in being mindful of what we eat regardless of size or weight. Yet, this question impacts you as a whole, your life, and your goals that supersedes dating.
Be vulnerable. This can feel scary at first, but it is the only way that you will know if you are dating someone worthy of your trust and love.
I would argue that finding your bashert trumps sightseeing and as far as I am aware, couples are still allowed on planes, not just singles.
It is infectious and we become transfixed by our screens, and laugh and cry at the weddings of strangers who understand so clearly that a wedding is about marriage, love, and the future.
Dearest Minimizers, please, I beg you, listen to me. We know that there are varied levels of sorrow. But our pain counts. It matters, and it should be acknowledged.
It is specifically during sorrow that we feel happiness so acutely. It is then that we truly understand how precious joy can be. How fleeting it can be. We can see blessings so clearly and know that they are gifts that must be cherished.
When mazel and bracha are offered to you, say YES. Do not pass on a first. This is dismissing a gift that has been presented to you.
When we face hardship, we often refocus on what is necessary and right and leave pettiness behind. Perhaps now we can take to heart the objective that dating has always had- to get married and to build a bayit ne’eman b’yisrael.
Dating is a commitment. Both parties need to be fully invested and focused on connection, advancement, and the future. When things are going well, this is even more important. Taking an extended break now, can deter the progress that you have made.
When your family, the shadchan, or a friend, offers you information about a potential match - inquire about her home life and the type of house she grew up in.
There are a million reasons why a wife must forego “extras” because they are not able to cover the cost. But this is not low maintenance or high maintenance. This is life as we hope to work toward more comforts in the future.
You are now a girl in shidduchim. This means that everywhere you go and anyone you meet has the potential to help you or hinder you.
Health and exercise are not WHO you are. It is something very important to you. I must assume that there are other things that you value as well.
Someone who knows the person well, or even someone who has previously dated a girl or guy can be a great resource in learning about a potential match. However, a real understanding of a prospective date can also lack objective and may contain personal bias.
Yes, it is true that we must devote a huge amount of our time and energy to dating. Yes, we need to make dating a priority and be willing to accommodate the opportunities that come our way. Still, you are not ONLY someone who is dating.
I think singles everywhere can safely assume that when we encounter them, we are all truly hoping and praying that they meet their right match soon.
You have been blessed to meet your right match and you are now preparing to spend your lives together. Yet, now that the excitement of your dating and engagement has waned somewhat, you are feeling unsure of how to proceed.
You are in a difficult position. While I commend your commitment to meeting new people by attending events, the lack of a matchmaker seems to ultimately be slowing you down.
Of course, you could meet your future husband next week, but realistically you know that there is no timetable, and you can’t help but feel the road shift, leaving you waiting at the curb.
You are not the first couple to mesh differing backgrounds. Many have created families enriched by the flavors of both of their childhoods to create beautiful homes.
Even though he didn’t display any more “red flags” on the rest of your date, you are concerned that this behavior is not something you should ignore. Was this just a bad moment? Or was your interaction a forecasting of a turbulent future; a discussion that must not be ignored.
Even when we are comfortable working toward a future with someone, we can feel blindsided by our date’s easy understanding of what a lifetime together would look like.
Let’s discuss the possible solutions to the pressure you are feeling. Your family believes that a certain number of dates should determine an engagement. If you believe them – propose!
We don’t date in rom-coms, we don’t date in romance novels, and we don’t date through insta-stories. We date in reality.
Kudos to you for seeing past an outfit on your dates. You knew immediately that here in fact the clothes don’t make the man” and you understand how precious his character and good middos are.
Yes, a Pesach program can be a wonderful opportunity for you to meet new singles. For those who are up for it, it can be a helpful gift in a dating journey. At the same time however, you need a break. You need the time to rest and you need the time away.
In a world obsessed with fame we must fiercely protect ourselves from the smoke and mirrors that is social media.
As you get older, the circle of potential guys becomes smaller and smaller. While there might be eligible men from a similar background that you may not have met yet, the possibilities grow smaller every day.
You feel maligned by the raised eyebrows and funny looks. May I be so bold as to suggest that their reactions are merely surprise at your good fortune?
She did not have anything negative or worrying to share about him. Yet, you are still thinking about walking away from a guy that sounds like he might be the right fit for you.
Time to take a step back. This is the time to refocus and to take your dating story back into your own hands.
Even if this trip is just for the sake of fun, it still holds merit.
I would never suggest that someone “settle” for someone who lacks mentchlichkeit. I would never want a girl to date someone as a last resort or without the confidence to say no.
They accuse you of being a fat girl masquerading in a skinny girl’s body. While this is clearly ludicrous, the hurt and stigma are very real. You are thin. Isn’t that what they want?
You don’t want to date someone who isn’t skinny and don’t understand why those around you bristle at that statement. Would they prefer you date a girl you are not going to be attracted to because of her size?
To have him suddenly make an appearance in your life again must have been jarring, forcing you to relive the emotions you thought you had put to rest.
Tell them you have something to share with them and then calmly relate the truth. Apologize for not being forthcoming until this point and take ownership of this slight and the hurt your secrecy will have caused them.
Dating is real... There is no thunderous realization while standing in the pouring rain, no chasing a plane as it is about to take off, or any other love cliché you can think of.
It bolsters us to hear that more than one or two people believe you would connect. This is especially true when everything else we learn, as far as character, personality, and middos feel right as well.
We are all perfectly imperfect. When we start cataloging human beings for societal imperfections, we will always most definitely find something wrong.
If overall everything seems so great, you wonder, why would you walk away over something small? Sure, there are a number of those “small” items, but surely, they are fixable, workable, or not even applicable in the near future. Still though, something doesn’t feel right.
For an introvert, a date can feel like a huge obstacle that they are unable to scale. There is a lot of talking on dates.
It's always exciting to start dating. At the same time, it can be overwhelming and daunting to make sense of the wonderful options of girls that come your way. There can be an element of uniformity to the resumes that makes it difficult to find the right one for you.
It would certainly be helpful if we had a clear picture of exactly when we might meet the person we will marry. A marking on a calendar would allow us to schedule our lives just so – with time to accomplish personal goals while maintaining a clear path for someone new.
We can only assume that up until this point you have been pleased with your chosson, his qualities, and his character. Yet, over Sukkos, he drank one night and you are now questioning your whole future.
If, however, you are happy to give someone a second chance at a date, you do not box yourself in with lists or refuse to continue dating someone if he doesn’t meet your extensive checklist, and you know specifically why you did not connect, then you can rest assured.
I wish you would have asked about a physical attribute, a speech impediment, or a height disparity. I would likely then have cautioned you to keep an open mind and to stretch your inherent beliefs.
A marriage filled with checks and balances and the need for an even playing field is always a recipe for conflict and resentment.
Dating can be daunting without the added pressure of seeking “kindness” above all else due to a difficult background. Of course you are looking for someone who is kind after your experience at home, as you hope to create a more peaceful life for your future family.
This is not a dating problem. This is a life problem. Being a people pleaser is nice, until it makes you feel resentful and not productive.
You are concerned that even if you are blessed with a “yes,” she may not like you after getting to know you better, and awkwardness with descend on both of your families forever and ever.
Unless you neglected to mention it in your question, I will assume his is not a mind-reader, a clairvoyant, or have telepathic powers. He cannot see your thoughts.
First dates are often fraught with nerves and there are those that are simply unable to put their best foot forward. This small window allows daters to barely scratch the surface of personality, temperament and shared interests.
Meeting the right person and a successful marriage will definitely infuse your life with happiness. Dating and marriage, however, are not the “cure-all” for all sadness.
Carefully and respectfully raise this issue again. Explain to him that while your salary might be higher than his, your earnings would be used for your collective family.
I would be remiss if I didn’t take a moment to mention that while I could never condone hurting someone’s feelings, the truth still matters.
Taking the time to reach out to those who know a potential date will offer insight into personality and character traits before you even meet them.
You have been blessed. You met someone quickly and forged a strong connection with ease. There are however, some guidelines that you can remember to reassure yourself that you are making a healthy decision. It’s all about the C’s.
Controlling behavior is always a red flag. A healthy relationship includes compromise and at the very least a willingness to listen.
You want to make a life with this wonderful guy, but you worry that when he sees where and how you have grown up, he will think less of you, less of your family. You feel ashamed.
You need to recognize that while you like each other and see promise in a future together, something in one or both of you is preventing an emotional connection from developing to the point that you can commit to one another.
We can perhaps discuss the importance of honesty. You did not give your sisters the chance to accept your choice with dignity before you began dating.
It is frustrating to feel like an afterthought. While I would like to give your date the benefit of the doubt and assume he most certainly wanted to be there, how he presented himself made you feel otherwise.
I have said this before and I will say it again; if someone cannot commit to you after a year, they are unlikely to commit to you ever.
While there are definitely older singles who are doctors, they are not standing en masse waiting for accomplished women outside the Emergency Room.
We can always argue that we only need that 'one' right person, but we still need to be offered the opportunities to meet that special guy.
You friend is not expecting you to pull a perfect single guy out of a magic hat. She does however, want your care, concern, and friendship.
How you present yourself is key. Both your character and your appearance should be refined to reflect who you are accurately and to your highest standard.
Please don’t think I am minimizing what you feel, but you must immediately expand your circle, your horizons, and your world.
You are doing so well. Dating is a challenge that often feels like a race without rules. Perhaps now is the perfect time to breathe and regroup.
Of course, you are intimated and overwhelmed. The more focused you become on their bottom line, the more bargain basement you will feel.
There is always safety in numbers. Travel with a friend or two and agree to look out for one another and to travel back to your homes together at the end of the evening.
You get along and have not found any distinct deal-breaking flaws in one another. But marrying someone because they are just “fine” is not a kindness to yourself or to them.
August 21, 2026 
