Category Archives: frumster files

Heinous or Harmless – Hair Covering and Dating

I have a friend “Roni” who was unfortunately widowed a while ago. She is the mother of young children trying to bring them up as grounded as possible, without a husband at her side. She has finally decided to take the plunge back into the dating world.

Roni is religious, and has continued to cover her hair (mostly with hats and scarves, occasionally a wig). She has spiritual and communal reasons to do so, and is not looking to change that. If she wanted, she could probably get a heter (rabbinical dispensation) to uncover, but she doesn’t want to, and is not interested in it at all.

She recently started dating a nice young man, someone who had never been married before. A man willing to take on her children and to follow a good solid marriage. A tall order!

But the hair covering thing is an issue for him. Officially, he says that he feels that this is a decision left to the woman he marries however on their first date he immediately asked Roni why she still covers, and was concerned that if someone he knew saw them, they would think he was out with a married woman. Roni tried to explain her feelings and conflict to him as best she could. She thought it was tabled.

In her words:

During our last conversation, we really shared a lot and I finally began to feel like we were becoming more comfortable with each other. I was getting high hopes for our third date, which would clearly be more relaxed and maybe help me sort out my feelings about him. Then at the end of the conversation, he asked me if I would consider not covering my hair while out on dates. I told him I needed to think about it, and maybe even consult a Rav.

But here’s the thing. I don’t want to go out in public with my head uncovered. I don’t feel like I am “there.” Also, I find inconsistency in observance due to circumstance to be inauthentic. I know women who don’t cover at work or on vacation and I have always felt it strange and didn’t get the rationale. But I don’t judge them because of how personal this issue is. It is a really hard Halachah for some, and I give them credit for what they are able to do. But to take a stance of I only cover [going to shul, doing carpool and getting groceries] or I don’t cover on dates, doesn’t sit well with me.

Roni asked me what she should do – she likes the guy. He is decent, there is some chemistry, he’d be a great male role model for her kids. But the fact that he asked her to uncover her hair when she is with him in public really poured cold water on the whole deal.

So dear readers, was this heinous or harmless on his part? What would you advise Roni to do?


WWYD – Shidduchim / Marriage

Shamelessly taken off a messageboard:

A kallah [bride] asked me to post this and solicit your opinions.

The kallah is in her late 20s, and smoked 1/2 a pack a day from age 13 until just a few weeks ago. Does she have to tell the chosson [groom]? She thinks he might have noticed, but they have never discussed it.

(p.s. There is no “warning signs” to be seen here. She just wants to do the right thing. )

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Medical Reports in dating – Heinous or Harmless


Can I see a medical report about your sexual / emotional health? Is this an appropriate question when dating BTs?

Is this done? Is it offensive? Is it considered a reasonable request?

Is it taboo to talk to a date about their previous sexual history, what kind of people they’ve had relationships with, what happened, did they get their fingers burnt, did they need therapy, did they get so badly grossed out or hurt by a previous partner that they now have fears, anxieties or inhibitions, did they ever get raped by a previous partner or some other random party goer? Was the rape first degree, second degree or what? Did they ever do drugs? Are there any long term consequences of their drug use?

I just read the above paragraphs on and I am a little disturbed. Obviously the person posing the question feels that this is something that should be done. I think my issue with the question is if you ask this of BTs, you have to ask of ALL the people you date – BTs, FFBs, converts, everyone. Don’t discriminate. But I am not even sure if this is appropriate at all. Thoughts?

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WWYD – Two Timer

Your friend is dating Mr X. Seriously dating, as in talking marriage. You happen to hear from somewhere else that the same Mr X is actually dating someone else as well, in a different city. Upon further investigation it becomes obvious that he is two-timing both of these women. Do you tell your friend? Do you tell her he was seen with someone else in a different city and offer to give her the number of the person that knows the other woman he is dating, for verification purposes? Do you stay silent? Do you tell yourself it is none of your business but gently hint that he may not be right for her?


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Matchmaker frustration

Long time reader and commenter Sheldan sent me the following last week. I decided to post it in its entirety so the rest of you could also read and comment.


This Shabbat I was reading the April 2 issue of the Jewish Press and the “Im Yirtzeh Hashem…By You” column.  Here is the article in its entirety:

Dear IY”H:

I wasn’t super-young (not in my 20s) when I got married, and thus was in the singles scene for quite a while.  I am no longer a newlywed, but still at that happy stage–as I am so thankful to finally be married.  But I am still not so far past my single days that I have forgotten all the drama and woes of being single.  With those facts as background, I try as much as possible to be involved in shidduchim on a volunteer basis.  I have been on committees for singles events, and everywhere I go I meet and speak to people, trying to get a sense of what they are looking for.

A while back I met a sweet young girl and her mother at a simcha, and a few months ago I met a woman who is looking for a shidduch for her son.  Based on what I know of the woman, I figured that if the boy is anything like his mother, he might be a good shidduch for the girl I met at the simcha.

As per standard procedure, I was to get the girl’s information and pass it on to the boy’s mother so they could begin looking into the prospective shidduch.  But when I called the girl’s mother, she refused to give me the needed information.  She wanted me to first give her the boy’s information because, the thinking goes, why should they even start the process if the mother hears something and decides that the shidduch is not shayach.

I agree, but usually the boy’s family first makes that determination.  I explained this to the girl’s mother, telling her that the boy’s mother does not want to put any more effort than her into this possible shidduch that may not be shayach.  I added that since we’re on the phone anyway, and since this is the way the things are generally done, I would like some basic information about the girl to get the process started.  And besides, if she wants me to have her daughter in mind for other boys, I would still need that basic information.  After all, how can I think of boys for her when all I know about her is what she looks and sounds like, along with a very basic sketch of the personality type she is looking for.

Once I put it that way, the girl’s mother seemed to be more willing to comply with my request for her daughter’s “shidduch resume.”  But then she said that she was in the middle of something when I called, and that she’d get back to me with the information I requested.  Months later, I’ve yet to hear from her.

I did not call the boy’s mother for her son’s information (to share with the girl’s mother) because that is simply not the way things are done.  I figured that if the girl’s mother were serious about finding a shidduch for her daughter, she would have gotten back to me.  After all, she has much more to gain from this than I do.

My time is limited and I am not being paid for this.  I have my own life and obligations, as well as other calls to make regarding potential shidduchim.  Am I asking too much by seeking people’s cooperation with me, especially when I am merely following common protocol?

I am beginning to think that parents’ lack of cooperation is a major contributing factor to the growing numbers of “older” singles, with the age of being considered “older” constantly getting pushed back.  (When I was younger, a 22-year-old girl was considered “starting to get older” whereas now, 22 is considered young.)

If volunteer shadchanim like me, who expect nothing in return, are met with resistance by the singles’ parents, it is not such a great mystery as to why girls are 22 and still single.

Having married later in life compared to my peers, I try to be a little bit more understanding regarding the plight of singles.  It seems that singles do not have a chance for success because they do not even get to go out in the first place.

What are your thoughts on this issue?  My strong reaction may be going a bit too far–but can you blame me?  Wouldn’t you be frustrated?


A Wannabe Shadchan Who Feels Unwanted

[Sheldan] After thinking about this letter, I suddenly had a strong reaction.  I don’t think I am comfortable writing back to IY”H, but I think I would feel comfortable in a forum like yours to air this.

This is my opinion:  When I kept reading about “standard procedure,” “the way things are done,” and “common protocol,” I got the same reaction that former Indianapolis Coach Jim Mora had when someone from the press asked him to comment about his team’s chances of making the playoffs:


(In case your readers didn’t catch the reference, I am sure that it can be Googled, and there was a commercial for Coors beer that lampooned Coach Mora’s response.)

Somehow, my brain kept screaming, “PROTOCOL?!”

To the letter writer:  The more I think about what you are writing, I think that you are well-meaning, but your insistence on doing things “the way things are done” is actually interfering with your chances of success.  Several times in the letter, you kept insisting that since “this is the way things are done,” your prospective shidduch’s mother should automatically do things your way.

If you are asking if you are asking too much for demanding that people “cooperate” with you exactly as you define it or you will not pursue it, I would say yes.  I think that harping on “the way things are done” shows little respect for the way the parents think things “should be done.”

First, if the shidduch is not shayach, what difference does it make which side put more effort into research?  The girl’s mother has every right to find out the same information about the boy that the boy’s mother has to find out about the girl.  Maybe the girl’s mother thought, “I’m not going to put up with this youngster’s demands that I do what she says–if she won’t cooperate with me, then I can find plenty of shadchanim who will.”  In other words, you assumed that the girl’s mother couldn’t do without you, which is arrogance on your part.

You state that “It seems that singles do not have a chance for success because they do not even get to go out in the first place,” but you also blame the singles’ parents for why “girls are still 22 and single.”

I think that maybe you need to rethink your ideas about “the way things are done.”  We don’t do things the same way as the 1950s, the 1900s, the 1850s, or the 1700s.  I think you unwittingly, when you refused to bend to the girl’s mother’s request, prevented the shidduch from taking place.  Maybe it may not be too late to do something about it.  If you explain that the shidduch depends on both sides giving the information equally to the other, I think, if the mothers are aware, they will consent to a mutual exchange of information.  Shidduchim do not need to be blocked by anything if they are truly beshert.

While I composed this, I had another thought.  I know that in a different era many Jewish girls got married by 22.  But it seems that nowadays, claiming that a 22-year-old is “older” is a bit much.  If anything, I would argue that the mid-20s might be the best time to get married now (and if singles stay single into their 30s, 40s, or beyond, I would be happy whenever they get married).  But in full disclosure, I have not been a part of the shidduch system and I do not claim to understand much about it.  I know that your readers may be more knowledgeable about the shidduch system than I and could explain it to me.

Therefore, I think this would make a good subject for your blog.  You may use as much of it as you like, should you choose to use it.


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Heinous or Harmless – Dating


Dear Editor,

My heart is so broken. I have been carrying a bleeding heart for over a month and cannot withstand it anymore. I do not want to tell my parents nor friends what I did, lest they make fun of me, yet I have to unburden myself, so I will tell you, on Matzav, what has been eating me up, killing me, and torturing me for the past month. Matzav has spoken to me about what I will share here, but unfortunately, to protect my privacy, I have to withhold my name from all of you.

About a month ago, my best friend living in Eretz Yisroel – for shana rishonah [first year of marriage]- called me up and said that this past Friday night, they had the most perfect suitable bochur for me sitting at their Shabbos table. He is learning in Yeshiva ______ [removed by editor] in Eretz Yisroel. She said that before I fly all the way from New York, I should talk to him over the phone, get to know him, and then, if things are okay, make the huge trip.

I agreed.

The boy called me up the following week and we hit it off real well. As a matter of fact, the phone conversation lasted a good two hours. We arranged another phone date. That one lasted for a good five hours.

I couldn’t believe how smooth the conversation flowed. We both found it very enjoyable to talk on the phone and decided that after just another three more calls, I’ll book my ticket.

The next two conversations were also wonderful. Then, during the second to last conversation we had, the boy indirectly requested a picture of me, only to get a better idea. By that time, I felt very comfortable to send him a picture of me.

The next day, I just couldn’t wait to hear from him and what he thought of me, because, after all, pictures can sometimes say a lot.

Soon enough, he called me and thanked me for sending a picture. In my head, I interpreted that to mean that he was impressed by my picture. But then he started telling me how boys tend to be very gashmiyusdik [focused on physical] and how it is very hard to look beyond the physical.

Honestly, I started shaking. I couldn’t believe what I was hearing! What?!

But I continued to listen. He went on to explain that I am a very wonderful girl, an excellent Bais Yaakov girl, etc. As he was rambling about my middos [good qualities], I couldn’t believe what I was hearing! After almost 16 hours of pleasant phone conversation, you are willing to say no because of my picture?

My heart was pounding. I was numb. I never, ever felt so degraded, so low, so cheap!

He ended off by saying that even though he’s not so much into my picture, he will overlook it because I have fantastic middos.

I told him that it’s okay. I wished him much luck and hung up the phone.

That night, I cried myself to sleep. Actually, for the next month, I cried myself to sleep, not because he didn’t think I was pretty enough, but rather because of how degraded I felt!

And now I turn to you, the mothers and fathers of boys. What are we teaching our kids? Who do you think you are to dare request a picture?

[Name Withheld For Privacy]

A Bleeding Heart

New York

HSM: So folks, is the bleeding heart right? Was the guy wrong for saying he will overlook her picture? Should he have waited to meet her before saying something negative about the way she looked? Should he have requested a picture before calling her? Is she right to be so upset? Was she right to not let him continue even if he was willing? Would you date someone without seeing their picture first? Did he give her false hope or is he well within his rights to turn her down based on looks? Was his behaviour heinous or harmless? Was her behaviour heinous or harmless? Discuss…..

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WWYD? – dating

A single girlfriend of mine (please forgive me for shamelessly stealing your story but you did tweet it) was recently set up with a bloke. They had some phone conversations before they actually met, to see if there was really a point to meeting. The conversations went ok, but he used a word that offended her. He used the very bad N word to refer to a person of colour. It bothered my friend and she wondered if it was even worth giving this guy a chance after he said that. From what I remember English was not his first language, but in my book that is still no excuse.

My friend is a very sweet person and after some thought and discussion with trusted friends she wanted to give him the benefit of the doubt. Seeing as everything else seemed to have been ok with the guy she did agree to see him. It didn’t work out.

What would you have done? Would you have gone out with him? Would the bad language have been a total deal breaker? Would you have thought, like I did (I can be judgmental), that if someone can be so rude about another person that they probably don’t have good middot? (standards of behaviour) Would you have been Dan L’Chaf Zechut (give benefit of the doubt) like my friend was? Has this type of thing happened to you? How did you handle it?

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Slim Pickings

Just had a girlfriend bending my ear about the ridiculousness of the shidduch business. She said all the shadchanim (matchmakers) really want to know is the size of the girl – slim, average or forget-about-it. Is she pretty? Does she dress well? They don’t even bother asking about her middot, her character or personality traits. Is that not important anymore?

Are there no larger girls needing to get married? Are they to be forgotten about because they cannot squeeze into less than a 14? There are not so many girls who stay size 2 after they have kids you know!! No one asks if the boy is fat, or skinny or has pimples.

Why so much emphasis on size??

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How many did you date?

In recent conversations with a friend, who is in her twenties and married, she happened to mention that her husband had dated almost 50 girls before he met her, and she had dated almost 20 guys. I was kinda shocked. I mean, I dated too, but I didn’t count how many failures I had! It just seems like an awful lot, but apparently when you do shidduchim it’s common. Since that conversation I have been trying to work out how many guys I dated before each of my marriages. By dating I think I am supposed to count each first date. Not phone dates, or internet chats etc. Each person that I met in the flesh, as it were.  Just bear in mind I did NOT shidduch date either time.

So here are my numbers. First time around I was 20 when I got engaged. I had dated 7 boys including the one I married. Second time around I was significantly older and wiser and well entrenched in my 30s. I did a lot of internet dating as most of the eligible guys were in NY. But I actually went out with 7 and married lucky number 7. To me that’s a lot in 18 months of serious dating.

Do people keep some kind of a log? I am sitting here counting on my fingers, wondering if someone was so forgettable that I….forgot him.

So, care to share your numbers?

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My kids are in shidduchim!!

No, not mine. Not now, hopefully not ever. Yes, that’s right. I hope they find their other half by themselves without my involvement. They are good looking boys and very personable, so they won’t have any problems. I do everything wrong anyway so I would fail big time with the shidduch checklist.

Let’s see how I would fail as a potential Mother in Law:

First and foremost I am divorced from my children’s father. Major strike against me. I use paper plates; sometimes I use a coloured table cloth on Shabbat; I totally stack dishes at the table; I sing zemiros; I am a loud opinionated wench; I think women have an important place in orthodox Judaism – and it isn’t being barefoot and pregnant in the kitchen. (Wait a sec, barefoot isn’t tznius!!!). I serve gefilte fish on Shabbat; I wear a seatbelt in the car at all times; I don’t cover my hair in front of my boys; I watch movies and TV; I drink unsupervised milk; and I rock on to 80s music; I wear pajama pants at night; I let my boys use gel in their hair when they don’t have school. Oh. And I blog.

How would I measure up?

I have a tiny waist and can squeeze into a size 2 if I have to. And that’s after birthing 4 kids. (Why that should matter with having sons, I don’t know). My hair is covered, mostly with a wig, when I am outside the house. We keep kosher and Shabbat and Taharat HaMishpacha (family purity). I gave the kids a yeshiva education. I don’t lie or cheat or steal.

So many people that I know will say, I have kids in shidduchim so I cannot admit to that (whatever THAT is) in public. It will count against my kids. I can’t go to the movies with you because I have kids to marry off. I can’t breathe in public in case someone might see my chest rising and think I was being immodest and it would count against my kids in shidduchim.

Whatever happened to honest and true family values?!! Isn’t that important too when looking for a life partner?

So, dear readers, what other insane questions have you been asked or heard of when having kids or friends in the shidduch parsha?

Disclaimer: This post is semi-tongue-in-cheek. If any of my kids wanted me to arrange shidduchim for them I would. It is just meant to highlight the insanity that I believe has somehow contributed to the shidduch crisis today.

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