The Shy Student: An Adventure in Shidduchim

by Ross Kryger

Every character trait has its benefits and detriments. On my very first day in Israel, dressed in shorts and a T-shirt, I decided to visit a popular tourist site called “The Wailing Wall” (whatever that was). Glancing around, I was intrigued by so many people praying outdoors, and although I wondered could be on the other side of this impressive structure, my eye was on the ramp. What could be up there? I thought, totally unaware that my “invisible impurities” presented any type of barrier from my finding out. I slowly ascended the ramp, and when I almost reached the top, I was suddenly halted by an exceedingly tall man holding a large brown robe. “In order to come up here,” he whispered in a rather demanding tone, “you must put this on.” I was confused, but I was also a bit shy by nature. I did not ask the reason, and I did not want to put on his robe, which anyway was about three sizes too large. I looked downward and subtly shook my head, then turned away and quickly returned to ground level. I remember that months later in yeshiva, upon hearing an Eliahu HaNavi story, I thought about this strange man.

My best friend landed in a BT yeshiva two years before I arrived in Israel, and although I now accepted his invitation after graduating college to visit him, I had no desire to meet his other orthodox comrades. Being a shy stranger in a strange land, I stuck closely with him, and eventually started paying attention to some of the ideas I was learning. I extended my stay (from two months to just over four years) and for the first eight months, we spent every Shabbos together. I was friendly to everyone in the yeshiva and made a few acquaintances, but after my best friend transferred to another yeshiva in a different town, I felt lost. While it didn’t affect my learning all that much, I wasn’t able, on my own, to gain the emotional support I sorely needed. My family at home was understandably hostile over my absence at my brother’s church wedding, and my decision to remain in Israel during the Gulf War sent matters spiraling downward.

I was never one to make conversation easily. I was the Haggadah son who didn’t know what to ask, so I rarely had any occasion to approach a rabbi about anything. The rabbaim were always friendly and polite, but I was missing that necessary deeper connection. Many times I would notice another student sitting at a table and talking with a rabbi for an hour or more, wondering what they could possibly be talking about, and feeling a twinge of jealousy over not having the same attention. Even learning with a chavrusa was somewhat difficult. Although much of the time I understood the basic meaning in the Gemorrah, I never offered an argument or a different perspective, but rather found myself nodding my head to any type of logic presented (perhaps to some guys, I would be a dream chavrusa!) Hillel says in Pirchei Avos that a student who is too shy will never learn, and I certainly have no doubt that I missed out on countless opportunities.

By far, the parsha of shidduchim was the most difficult. After noticing for a while that guys who have been in the yeshiva as long as me were either getting engaged or actively dating, I approached a rebbe who knew somewhat of my family circumstances, and sheepishly asked him when I should consider starting. He stared at me incredulously and said, “You’re not dating yet?!” The words, “I was waiting for you to tell me when and how to begin” luckily didn’t escape from my mouth, as the last thing I needed was a rebbe who thought I was full of chutzpah. He then gave me the name of a few shadchanim and their addresses, and told me I could later give him a name to check out. I was a little curious that he didn’t discuss with me about the process in general, or even if I was ready.

Most shadchanim smiled when I informed them that in my “former” life, I never had a girlfriend (it seems my shyness turned out to be an asset after all.). Although they offered me names of girls from all types of families, I was most excited to hear the names of BT girls. I really wanted someone who could understand me, and where I was coming from in life. She would have a spiritual side, and we could grow together. (I’ll give away the ending—I married a wonderful FFB, but the contrast in our married life is for a different article, perhaps.) The first name I received was of a BT girl, and I passed it on to my rebbe, who told me to go out for now, and he would check her out. The shadchan set up the date, and I just needed to take a bus and meet the girl at a hotel. What a great system for a guy like me! On the designated night, I was a little nervous, and arrived at the hotel. There were four girls standing outside. They all looked at me, waiting for me to do something. Since I couldn’t pick out the girl myself from the lineup, I was at a loss for the proper protocol. Luckily, one of them finally decided with a grimace that I just couldn’t be her date, and walked away (well, excuse me!) With great embarrassment, I chose one of the remaining three at random, and stammered, “Are-are-y-you Sh-sh-shoshana?” “No, I’m not,” she replied firmly. I was somewhat relieved, as she was about five inches taller than me. The real Shoshana slightly smiled and introduced herself. She seemed to be knowledgeable in this system, as she explained that this happens quite often. We left the final contestant outside (presumably brokenhearted) and found a quiet table in the lobby.

I sat down, and she sat down. I nodded, and she nodded. I smiled, and so did she. How long was this date supposed to be? I really don’t know what I had expected a date to be like, but pathetically, guys like me need a manual. Was there one under the table? Little did I know that I was expected to…talk. And talk. Certainly not my area of expertise. The date was on the short side (I know it was, because when we left the hotel, contestant number three was still waiting for her date). The next morning, I was more than a little surprised when my rebbe quietly remarked, “The date was how long?” But I must have done something right, because she agreed to go out again. Then the floor completely fell through. My rebbe informed me of certain information which might effect this shidduch, and advised me not to continue. I had no problem with that, but then I stupidly (!) passed this on to the shadchan, and somehow it got back to the girl who traced the information to its original source. I still remember the dreadful conversation with that rebbe, who was understandably livid, to say the least, and hinted that I should find someone else to consult with. I was devastated. (Not to mention disgusted over the pain I must have caused the girl.) And now I was totally alone. This was my introduction to the world of shidduchim.

After a break, I did start dating again, but every date was so exhausting, and keeping the conversation going was worse than heavy manual labor. Things would inevitable fizzle out. I also had nobody to talk to in the yeshiva. In addition, it was very hard for me to say the word “No” to a shadchan. It was all quite confusing. Soon after, I made a decision to return to America, and entered a yeshiva in Brooklyn, far from my hometown. My issues with shidduchim followed me there, and to make matters worse, I actually had to call the girl before we went out! There were guys who told me that they spent four or five hours on the phone with a girl, and I couldn’t imagine how this was possible. (I once spent two hours on the phone, but that was when my insurance company put me on hold.) And then, after an actual date, I had to make the decision, of course, by myself.

Another problem which came up is that I began to develop stereotypes. Even though looking back, I feel that every girl that I dated, without exception, was a special person, I really did not feel that a Brooklyn FFB girl would be able to understand me at all. For whatever unfortunate reason this came about, I really did not want to pursue such a shidduch, but again, I found it too hard to say “No”. (It would be a great punch line to say that my wife is from Brooklyn. She’s not. Sorry.) Overall, my career in shiddichum lasted for six long years. Luckily, I never became depressed or despaired, although I couldn’t figure out how guys became engaged. It was like a huge mountain. When I did finally become engaged, I saw that the whole process entailed enormous siyata d’shmaya, and I guessed that up in Heaven, they were tired of watching me go through this.) The first few dates were quite a lot of work for me, but I just kept plowing through. On my last date, we were driving through my hometown, and she casually remarked, “If you’re waiting for me, I’m ready.” I grasped the steering wheel. It was the closest I ever came in my driving career to hitting a tree. We’re now married with six children.

Everyone knows that the biggest rule in shidduchim (besides serious davening) is that one must have someone with whom to consult. In BT yeshivas, a guy is fortunate if he makes that vital connection with a rebbe with whom he feels comfortable. If the guy feels the rebbe understands him, then he’ll take the leap of trust in the rebbe’s judgment, even if it seems that he personally would do the opposite of what the rebbe says. People do make mistakes, but a guy must trust someone, and as my Rosh HaYeshiva once said, one has siyata d’shmaya when he listens to his rebbe. But not everyone is so lucky, especially guys like me. Sometimes it’s not easy for us too search out the help we need. We find the same occurs in school age kids. Many times, a rebbe might not concern himself with a student because it seems like he’s doing just fine…he never complains, he does everything right, and he sits so quietly in class. How many students have fallen through the cracks because in reality, they were not doing just fine, and could’ve have really used some attention? Many are just ashamed to ask. Guys in a BT yeshiva are like school age kids. They’re in a somewhat new environment, and are learning just like the school age kids. And they all need attention, especially when it comes to shidduchim.

The yeshiva must make sure every guy has appointed to him a mentor or a rebbe when he begins to date. Every guy must be accounted for, everyday of his yeshiva years. (There must also be a service provided through an organization for single guys who are not in yeshiva, or living on their own). Sometimes you have one rebbe whose job is too deal with shidduchim, and guys need to make appointments to speak with him. But that’s very hard, because after a date, a guy needs someone to speak with NOW. Having hanging indecision for a lengthy period can also be detrimental.

The fact is that practically, there aren’t too many solutions to this problem. But I think that everyone who is employed a BT yeshiva should, before he goes to work, sit on the floor with his legs crossed and eyes closed (like the Jews in India before they discover Jerusalem and yiddishkeit) and repeat over and over, “He has no family, he has no support, he is alone.” Or can they can just repeat this mantra in their heads while surveying the beis midrash and finding at random a guy to shmooze with about his life. Even if the guy seems he’s doing just fine. BT yeshivas are filled with rabbeim who understand human nature and can guide others according to the Torah, and everyone should have strong connection with one.

As we watch our families grow, may we always merit the proper guidance and may we only share simchas together.

Originally Posted July 2009

32 comments on “The Shy Student: An Adventure in Shidduchim

  1. Tevya, I’m sorry that I did not respond before, I actually didn’t know about BeyondBT until well after the time of your posting.

    My husband and I live in the Bayswater section of Far Rockaway. If you still work in Cedarhurst on Friday, we would be honored to have you as a Shabbos guest. I actually also work in Cedarhurst on Friday and Sunday, so that I could actually meet you in Cedarhurst and direct you to my house in Bayswater on Erev Shabbos.

    We would be honored to have you join us for this upcoming Shabbos, Parshas Zachor, unless you have made other arrangements for Shabbos & Purim. Please contact me at my email to say Yes or Not This Week But Maybe Another Week to this invitation. Looking forward to hosting you for Shabbos.

  2. Ross,

    Where are you living? I have a feeling you live in the NYC area. I work in Cedarhurst Wednesdays and Fridays and in Staten Island on Tuesdays. Also, I cannot be proactive in this. I was hurt too many times by people. I even had chavrusas from PIT and it stopped. I personally feel that the frum community does not care about other people except for the people that are amongst themselves. Please do not be offended by this but if you are in the NYC area, do you or know of other people that do have guests on Shabbos and Yom Tov and are willing to bring them closer to Torah and make them feel accepted? I ask not only of myself but also to make you realize that you should go up to people and make them feel welcome. It is always easier if people are welcoming and I have experienced the opposite unfortunately.

  3. Hi, Tevya. Meeting me is not such a big deal and hardly worth going to an organizational dinner for, especially considering what they charge for parking. But thank you.

  4. Bob,

    No I am not making Aliyah at all. Isralight teaches the spiritual truths of Judaism. They are right near AISH HaTorah.


    I love what you wrote here especially #3. I would have a chance to have met you at the Agudath Israel dinner this year. I was invited by a friend from SI and he told me that if I wanted to go to Passaic for a Shabbos he would contact you. Anyway, I didn’t go to the dinner because I could not afford it but I heard it was nice.

  5. Oh, maybe one more, on reflection:

    4. Someone who is the subject of (1) and nonetheless, in his or her idealism, submits himself or herself to (2), is especially entitled — yes — to the benefits of (3).

  6. Thanks, Mr. Cohen.

    I do think we can say a few things:

    1. In life, being painfully shy is usually a big disadvantage.

    2. When trying to integrate into a different subculture or culture, a painfully shy person is at risk of making his or her “handicap” even more of one.

    3. In a subculture such as orthodox Judaism as we know it, which posits chesed [kindness] and ahavas yisroel [love of one’s fellow Jew] as prime directives, members should be particularly sensitive to (1) and (2).

  7. Bob,

    That is true that I need to do something but I cannot do anything if I am made to feel like an outsider amongst my own people. Anyway, on a more positive note I will be in Israel tomorrow until August 2 on a Isralight Inwardbound trip. So I am doing something which I hope will give me some answers to questions that I cannot ask here due to the coldness of the frum community here in NYC/NJ.

  8. The shuls in Elizabeth NJ are primarily in one network, the JEC (Jewish Educational Center). In the mid 1990’s I needed to spend a Shabbos there while ona business trip, and called the office. They easily matched me up with a family. I also knew no one going in, but had a great Shabbos anyway. You can, too, but you need to do something.

  9. Bob,

    True but I do not know anyone there and I am not going to call any shuls there. Thanks anyway.

  10. Bob,

    The only problem with the Highland Park community is that I am in Cedarhurst on Fridays late and I am not driving out there. But thank you for the suggestion.


    Why didn’t you respond back to me? I am sorry if I made you feel uncomfortable if I did.

  11. Ross,

    Where are you living? I have a feeling you live in the NYC area. I work in Cedarhurst Wednesdays and Fridays and in Staten Island on Tuesdays. Also, I cannot be proactive in this. I was hurt too many times by people. I even had chavrusas from PIT and it stopped. I personally feel that the frum community does not care about other people except for the people that are amongst themselves. Please do not be offended by this but if you are in the NYC area, do you or know of other people that do have guests on Shabbos and Yom Tov and are willing to bring them closer to Torah and make them feel accepted? I ask not only of myself but also to make you realize that you should go up to people and make them feel welcome. It is always easier if people are welcoming and I have experienced the opposite unfortunately.


    The shuls here in NYC do not have a hospitality chairman at all. It is a very closed off community here. People have said to me I should in a out of town community but I do not know where.

  12. When I took a job in Houston, far away from any family members, it was about 6 months before my wife and family were able to move there to join me. In the meantime, with the help of the shul’s hospitality chairman, I was invited for Shabbos meals (various homes) virtually every week. I was living in an apartment within walking distance of the shul, so I didn’t need overnight accommodations, but I’m sure, knowing the people involved, that those would have been taken care of, too. Once we had our own house inside the eruv, we were able to receive guests ourselves, often routed by the same chairman.

  13. Tevya–
    I remember when I first arrived at yeshiva and my friend informed me we were going to a certain rabbi’s house. “Wow!”, I said, “He must really like you to invite us like that!” You can imagine my surprise when I was told, “Well, no, I invited us to his house.” I was almost disgusted. “How can you do that?! I’m not going to a place I’m not welcome!” He laughed and made a comment about it being the “accepted” practice. On which planet? I thought.

    Tevya, to make a very long story short, it IS the accepted thing in orthodox circles to pick up the phone and say, “Hi, I was wondering if you are taking any Shabbos guests this week.” (In yeshiva, I was actually brainwashed to do this on Tuesday, believe it or not.) Nobody is offended by this, and you are not imposing on them, because it’s also accepted that if they can’t have you, they will say, NO. Then you try again, or as Bob suggested, call the shul. You meet people who WANT you as a guest, then eventually you end up with set families you enjoy going to and who enjoy having you, and will say NO if it’s not a good week, but “Please call next week.”

    But you must jump in and try. Take it from a shy fellow…this IS the way it is. Be proactive!! (And try reading The 7 Habits of Highly Effective People. It’s a great book recommended by many (!) frum people.)

  14. You have a right to ask them! They will typically be very gracious and obliging (As I said, the easy way is through a shul’s “hospitality person”.) You’re offering them a chance to get to know you and to perform a mitzvah.

  15. Bob,

    What do you mean “It takes two”? I live with my parents still and I do not live in a frum community so I cannot offer them anything. It is a mitzva for them to offer shabbos and yom tov hospitality for people. I have no right to ask them for it.

  16. Ross,

    Where are you living now? And if you are in the NYC community which community are you a part of?


    Yes there are two Young Israel shuls on SI. People know that I exist but they do not extend themselves and gives me a very cold impression.

  17. Tevya,
    I agree with Ross. No one can offer Shabbos hospitality, etc. if they don’t even know you exist. Nowadays, virtually every Orthodox Shul has someone coordinating hospitality. Maybe it’s the Rabbi, maybe it’s a member. To find out, call the main Shul number and either speak to someone or leave a voice mail to ask about Shabbos hospitality, service times, adult classes, and anything else of interest.

    Right now, I’m aware of two Young Israel congregations on SI, the big one in Willowbrook and a newer one in Eltingville.

    FYI, even when I’ve had to travel abroad, and I’ve called ahead to congregations where I knew nobody, I’ve always gotten a warm response about Shabbos accommodations.

  18. Hey, Tevya. Perhaps a good first step for you would be to either contact the Rabbi from either the Agudah or the Young Israel in SI, and just introduce yourself. If you’re painfully shy, then write a script, hold your breath, and go for it! The rewards are far greater then the discomfort.
    Or another idea would be to contact the Aish HaTorah on the upper west side, and again, just introduce yourself. I promise you that any of these mentioned won’t answer you with, “Yeah, so?” They are waiting to hear from people like you all the time, and can help you meet the right people, so that you can finally be included in the community! But the first step is YOURS…don’t point the finger, just pick up the phone. Oh, and most of all…pray with all your heart to G-d that you make the right connections so that you can grow as a Torah Jew!

    You won’t regret it!

  19. Some of the comments (1 and 8) address Shabbat meals for BT’s.

    Sometimes I call people before Shabbat and sometimes they call me.Sometimes I get spontaneous invitations, sometimes I show up spontaneously.

    However, I also do something that seems to be a rarity in my circles. I am a BT, who is divorced and on his own every other week, while on other weeks I don the single parent hat. Nevertheless, I very often make my own meals, whether my kids are with me or not, and I invite people to visit me for Shabbat meals, too.

    I have mentioned this practice to some other “older” singles in my area, and it seems that “we don’t do that around here.” Nevertheless, I have heard that it is a common practice in other areas.

    It is a part of every adult’s attainment of maturity to achieve the ability to enjoy a meal on one’s own or with one’s family, and to be a host to others in one’s own home. This applies to singles, marrieds, parents, and those with no children at home.

    There is no reason for a newly single or newly religious person to abandon the use of these skills.

  20. Mr. Cohen,

    Hi there. I love your advice for the frum people to invite BT to their homes. Over many years people tell me that I should invite myself and I cannot do it because I think it is wrong. And I feel that I am not accepted or wanted as part of the social circle of the frum world or BT world at all. And I feel that people on this site do not care as well unfortunately.


    Hi. I am also in a similar situation like you once were. I am a 31 year old single male from Staten Island, NY. I never went to a BT yeshiva but I feel that the frum/BT community here in NYC/NJ is very isolating and it hurts too much. I am a very shy individual who has trouble reaching out to people because I feel that I am an outsider. I do not have a rabbi or friends to consult with about anything and I also feel very lost. I am not shomer shabbos because people do not invite me to their homes and I am not involved in a community and I do not think things will change for me. I feel like I fell through the cracks unfortunately. I am happy that you got help. I just hope wherever you are living you are reaching out to your fellow Jews with ahavas yisroel which the FFB/BT community needs to learn to do with their non-observant brethren and people that want to come back to Torah. Hope all is well with you.

  21. The FFB world is so over-focused on getting people to come through the door (kiruv) that it tends to neglect those who have already been inside for a while.

  22. Perhaps you were blessed with this struggle in shidduchim in order to use your sensitivity to the problem to help bochurim in this dilemma now. Your advice for the rabbaim and yeshivas will hopefully be well taken, but you have the gift of hindsight and perspective from personal experience with which to assist bochurim-in-need yourself.

  23. Ross,
    You really write very well. As for the main point you seem to be making, it is not so simple. Baalei T’shuvah need to be SO careful to not loose their spontaneity and independence of thought.

  24. That is excellent advice. People deffinately need a good support system to help them along the way. You also have a good point that sometimes people who look fine, fall through the cracks because nobody noticed anything. On the one hand, it’s hard to know who needs more attention, and it’s hard to give each one that. However, it’s very important for teachers to have a good connection with the students inorder to help them, and keep them from falling.

    Secondly, I want to say that I admire your strength to go forward with your goal despite the difficulty. Some probably would give up, but then we don’t reach our goals. Your continuous effort and emunah has brought you far, Baruch Hashem

    Again, great post

  25. You make a few nice points here, Ross. Everyone in any yeshiva, but certainly in a BT yeshiva, should have someone from the hanhola [senior faculty] keeping tabs on him, mainly for his benefit. Because you didn’t make any trouble, no one was worried about you — you weren’t a “problem.” This was a mistake of management, i.e., hashgocha [supervision; here a play on words because of the allusion to the moshgiach, who has this responsibility in a yeshiva]. When I was in the bais medrash at Aish HaTorah in the late ’80’s, this was systematized to some extent. We even had regular vaadim [presentations] by the then-Moshgiach Ruchani, R’ Yitzchok Berkowitz shlit”a.

    On the other hand, there’s something to be said for eventually doing some growing up and bursting past your own limitations of personality.

    I had no guidance during the process either. Does everyone, really, or is that an ideal more observed in the breach than otherwise? As an experienced young adult I believed this was basically a decision I would have to make for myself.

    I believe one of the most useful things in this article is this passage:

    I think that everyone who is employed a BT yeshiva should, before he goes to work, sit on the floor with his legs crossed and eyes closed (like the Jews in India before they discover Jerusalem and yiddishkeit) and repeat over and over, “He has no family, he has no support, he is alone.”

    Not only people employed in a BT yeshiva. Everyone in the frum world who wants to be BT-friendly, BT-supportive, BT-accomodating — or, frankly, who just wants to avoid being BT-insensitive or cruel — should really ponder this truth. Most have no appreciation of this level of isolation (even if a sibling becomes frum too, though this is immensely helpful) from the social and personal support systems that they take for granted every bit as much as a healthy person does his basic senses. The effect does not wear off after 10 or 20 years, and it is not confined to the first generation.

    By the way, no one ever described me as an introvert, nor my wife as an extrovert. But my marriage proposal was elicited by my wife more or less the same way yours was!

  26. Ross Kryger has written an interesting article.

    May I add that Baalei Teshuvah are often dependent on others for the Shalosh Seudot of Shabbat, and it is often awkward for Baalei Teshuvah, especially those who are shy, to call an Orthodox family for the purpose of visiting that family for the coming Shabbat.

    REASON: From the perspective of the Baalei Teshuvah, this phone call may feel like: chutzpah or begging or invading the house of a stranger.

    It is very helpful when the Orthodox families make the initiative to call the Baalei Teshuvah to invite them for Shabbat.
    This maked the Baalei Teshuvah feel that they are sincerely wanted, not merely tolerated.

    Ideally, this phone call should be received by the Baalei Teshuvah on Wednesdays. Waiting until two hours before Shabbat to make this phone call may make the Baalei Teshuvah wonder why you waited until the last minute to call, but even this is better than not making the call at all.

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