Funny Shidduch Stories

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    Lilmod, that was a great story! But don’t leave us hanging for the cliffhanger.

    Who did he end up deciding to marry – Sara or Esty?

    Lilmod Ulelamaid

    So after Yossi finished laughing and apologizing, Sara told him that she would speak to Esty and they would decide which one should date him first.

    Sara and Esty discussed it and tried to figure out which one he would be most matim for. In the end, they concluded that he would be the most matim for their third roommate, Tova! L’maaseh, Esty went out with him first. I don’t remember if Sara or Tova ended up going out with him.

    I do know that none of them ended up marrying him. Esty got married to someone else, not too long afterwards. Sara got married around 15 or so years later. I have no idea what happened to Yossi or to Tova (whose real name I can’t even remember).


    Yossi and Tova eloped.


    It’s so nice that you guys have such cute stories! I only have experienced/heard sad stories… BS”D not anymore in future!

    Burnt Steak

    My friend set me up with a girl who he said would be a great fit for me. He wouldn’t tell me much about her except that she was a good girl ect… I talked with her on the phone and we had a good conversation. She told me she knew a few players on my favorite football team and we decided to go out. From speaking with her on the phone I thought she was similar to me.

    At the time I was living in Manhattan and she was in Staten Island. We were gonna do the date in lower Manhattan. I went to meet her on the Staten Island side of the ferry. She was late and missed the ferry. When I saw her I knew it would not work out. I was not attracted to her, she was very different hasgafically than me, and we had almost opposite views in life and wanted different things. We ended up walking around lower Manhattan and I decided to have some fun and asked her if she knew who Harambe 讝讻专讜谞讜 诇讘专讻讛 was. When I heard she didn’t know about the Great One, I spent the rest of the date showing her Harambe memes.

    I ended the date on the ferry ride back to Staten Island. Unsurprisingly she agreed with me.


    It sounds like the joke being made in BMYer’s story was that the reason the boy opens the
    car door for the girl is that they’re afraid the girl might damage it if she opened it herself.


    Any more?


    Thats it, no more?

    boki beshas

    Please tell me you bought her the shot glass that says “take a shot for harambe, he took one for you”

    Reb Eliezer

    Be careful roomates or sisters should not show up when it is not their date. The date might get derailed by him falling for the wrong person which is funny but it is not.

    Dr. Pepper

    This happened to our babysitter-

    She started dating fresh out of seminary and got pretty far with the first guy she went out with. He had mentioned to the shadchan that he was ready to get engaged and then reality hit her. She was having a good time on the dates and enjoyed being around him but she felt that she might not be mature enough to get married and take on the responsibilities of raising a family. My wife sent her to speak with a rebbatzin who agreed with her that she wasn’t ready to get married for some time. She then called the shadchan, explained what was going on and said that she needed to end it.

    A few months later she saw on a different website that the guy had gotten engaged.

    Fast forward some more time.

    She’s in Lakewood for Shabbos and hitches a ride back to Flatbush Sunday morning with a distant cousin who’s been married for a few years. When she introduces herself to the husband he has this strange look on his face and asks if she has any older sisters. She answers that she’s the oldest but is totally unsure of what he’s getting at. Then he asked if she has any female cousins with the same last name that are dating and she said that her father doesn’t have any brothers- but she is still unsure of what he’s getting at.

    During the ride she’s sitting between their two infants and entertaining them. When the kids fell asleep the husband starts talking and explains that he has a friend that had gone out with someone with the same last name so he just wanted to make sure that it wasn’t her sister or cousin. Since he already confirmed that it wasn’t her older sister or cousin he began to relate to her what this “horrible girl” had done to his friend. “She totally led him on that she was interested in him until he was ready to propose and then she claims that she’s not ready to get married.” So, our babysitter considers jumping out onto the Garden State but figures that the child safety locks are engaged and doesn’t even try. The guy keeps going on and on about how horrible of a person this girl was to his friend and she’s sitting there not knowing what to do.

    Finally she breaks the ice and says, “WOW, she really does sound immature! I sure hope your friend finds someone else right away and she stays single until she grows up a little”. She spent the rest of the ride sympathizing with the guy while trashing herself.

    Dr. Pepper

    This happened to a former student of mine (I heard it from him)-

    He’s driving her back after a great second date (the first one went great as well) when she asks if she can ask him some questions. He agrees.

    “So, thinking about your upbringing, can you relate to me a decision that your parents made that you agreed with and a decision that they made that you don’t agree with?”

    He was totally caught off guard and was speechless.

    She told him that if he didn’t have an answer right away she’ll go on to the next question and he can think about it and give her an answer on the next date.

    “So, thinking about your current chavrusa and a former chavrusa, can you tell me something that you like better about your current chavrusa and something you like better about your former chavrusa?”

    Again he’s caught off guard and is speechless. She again offers to go on while courteously allowing him to bring an answer to that question as well to the next date.

    Without looking up from the road he asked her if she鈥檚 reading these questions off a paper or something, but she said that she forgot the list of questions at home so she鈥檚 going by her memory.

    By the time he got to her house he hadn鈥檛 been able to answer a single question of hers but she gracefully allowed him to answer all her questions on a subsequent date.

    Unfortunately for her- there was none.

    A few weeks later I noticed that he wasn鈥檛 by the Mincha that we usually went to and his brother told me that he was on a date.

    I sent him a text- 鈥淪o, thinking about the girl you鈥檙e currently dating and a previous girl you dated, tell me something that you like better about this girl and something that you liked better about the other girl?鈥

    He texted back that they both found it hilarious. (They eventually got married.)

    Dr. Pepper

    Heard this from the person who it happened to during the shiva for her father-

    The niftar was a senior pediatrician from the practice that we use.

    One of his daughters related that after the levaya before the burial she was surrounded by her friends when a guy she recently broke up with popped out of nowhere and said 鈥淚 felt that I have to be here for you.鈥


    鈥淚 felt that I have to be here for you.鈥

    Did they get married?

    馃崼Syag Lchochma

    That is really awkward. I hope he didn鈥檛 show up to the shiva house every night

    Dr. Pepper


    I don’t know her too well and I have no idea who the guy is. They had already broken up at the time and I doubt that they reconnected.

    馃崼Syag Lchochma

    These stories just make me more frightened to send my kids out with 鈥渟trangers鈥


    Syag, your kids can marry their cousins.


    No one posted the one about the ultra frum BJJ girl who informs the boy she is dating that she asks people to call her 鈥滲aska鈥 so as not to pronounce the Shem Hashem by saying 鈥淏asya鈥. He replies 鈥渋n that case please call me Keilikaku鈥.

    I was told that the following took place with the parent of a friend of mine be a few decades ago. The boy was supposed to go out with this girl who he wasn鈥檛 thrilled about, and just before the date he was told that another girl who he was very interested in had become available. He figured he鈥檒l just act over the top and get the first girl to reject him. He gets to the house and and they offer him some cake. He says 鈥渃ake? I LOVE cake! 鈥淭hey offer him some Pepsi and he says 鈥淲OW! PEPSI! My favorite! And so on during the date as well. After the date he gets a call from the shadchan who exclaims 鈥淲hat did you do? He thinks to himself oh boy, I really rubbed them the wrong way. The shadchan continues, 鈥渢hey loved you! The parents and the girl are so excited and looking forward to the next date!

    馃崼Syag Lchochma

    Yzj- great stories!


    Did I somewhere within the over 1,400 funny shidduch stories posts on this thread over the past 10+ years ever retell the story of my date with Dr. Pepper’s sister?


    There once was a girl named Shprinszy,
    who I was to meet for a coffee,
    when I got to the hotel,
    I said hello, I believe you are Sprinkly,
    I mean Sherinsky,
    sorry Shrinky,
    I mean Sheprinsky,
    I am having trouble pronouncing your name Stinky,
    She gave me a look,
    and said that was enough
    and that was the end of that shidduch!


    Once I met a girl on a shidduch,
    Who had on pale makeup,
    Her lipstick was black,
    And her eyeshadow dark,
    And she was dressed as though she was ready for a funeral,
    I said hi there Devorah are you ok,
    And she said yes I like the cemetery,
    I said 鈥渁re you a goth?鈥
    and she said 鈥測es,
    there is nothing wrong with that!鈥
    Oh I said that鈥檚 fine I will be back at 9
    And disappeared before she could lock me in a coffin!




    After coming home from learning in Yeshivat Ohr Yerushalayim, my friend went directly to Lakewood to meet with a local shadchan.
    After explaining that his family is very Modern but he flipped out in OJ after graduating his co-ed high MO school, the shadchanit told him that he and his family were too goyish for the girls she knew.
    After a few more squabbles, my friend ended up marrying that shadchanit’s daughter.
    To this very day, she still thinks her son-in-law is a goy!!

    Dr. Pepper


    I just saw your question from last year. I don鈥檛 recall seeing the story anywhere except when I first posted it back in 2009.

    Reply To: Funny Shidduch Stories

    When I went back to that part of the thread there were some comments missing- including the one where you admitted that you were the guy she was dating. You can tell by the lack of continuity.

    My brother-in-law found out about it and still teases her. When they recently went food shopping and the grocery store said they needed to wear gloves he took two out of the box, stared at them, and said 鈥渓ook, they gave me two right handed gloves鈥!

    He doesn鈥檛 tease her about dating you though so he must not have found out about it by reading it here.

    馃崼Syag Lchochma

    Dr. Pepper- joseph hasn’t posted in over a month and with Covid-19 I worry about people when they go awol. There is no way he would miss out on responding to a post from you so hopefully we will hear he is well.

    Dr. Pepper

    Syag Lchochma-

    I checked on the profile for Joseph and it was obviously a different profile as this one was created less than 3 years ago and the original post was over 10 years old.

    (It may have been the same Joseph though.)

    馃崼Syag Lchochma

    Pretty sure they’re all the same Joseph. I checked a few joseph profiles but found nothing more recent than july 2nd.


    wow I cant believe the same people have been talking to each other on this thread for 9 years. Do you guys know each other personally? like, in real life

    Dr. Pepper


    For the most part I don鈥檛 know who these profiles are in real life. Every so often I figure out who someone is and so I let them know (just so that they don鈥檛 think they鈥檙e anonymous) but they usually deny it.

    In one case a poster called me a name in a different thread (I鈥檓 not sure if it was meant to be complimentary or derogatory) but I never heard the term before. I then overheard a coworker referring to an old colleague with the same terminology and put two and two together. I informed him that his covers been blown (I didn鈥檛 tell him how I figured it out) and he denied it but the profile was immediately retired.

    Joseph is a different story altogether. Given that the Frum, Yeshivish community is very small most posters who want to remain anonymous are careful not to let their guard down.

    On a different forum I noticed that a poster had some close similarities to Jospeh and started monitoring the posts from both of them. After I was totally convinced I ran it by another poster who I was in contact with in real life and he thought it was solid. At one point he slipped and let his guard down and gave away enough information for me to figure out what his real name is. Of course this may have been intentional to throw people off- I鈥檒l probably never know.

    Also, I can鈥檛 even be sure that the Joseph that I tracked down is the same Jospeh who鈥檚 posting nowadays.

    馃崼Syag Lchochma

    Oh boy, you got me so curious!!


    By the way, there are at least 7 joseph’s

    Dr. Pepper

    Syag Lchochma-

    It鈥檚 really not too interesting or worth losing sleep over.

    I鈥檓 going to try to give all the details but some of the posts I鈥檓 going to reference have disappeared over the decade so it鈥檚 hard to fact check.

    The first post from a 鈥淛oseph鈥 that caught my attention and was an inside joke that was going on at work and I showed it to a colleague of mine and asked him if he thought it was a different colleague whose name is Joseph. He agreed that the poster either worked with us or a competitor unless it was just a strange coincidence. After checking out the other posts by 鈥淛oseph鈥 we came to the conclusion that they were too radical to be from our coworker.

    Sometime later I was reading a post that I suspected was from a 鈥淛ospeh鈥 and he used a word not in my vocabulary that I had to look up in the dictionary. Around the same time I was on a secular (albeit professional) website where the same thing happened. Those are the only two times I recall having to look up a word in the dictionary that I came across in an online forum. Given that some of the interests that our 鈥淛oseph鈥 had coincided with the poster on the other site I began to follow the two of them very closely.

    I noticed another pattern in the two of them in that they both asked questions to new members that they seemed to know (or, based on proven expertise in a topic, should have known) the answer to. I don鈥檛 know what the point of this was, possibly to build trust amongst new members, but whatever it was- the pattern was clearly there.

    The poster on the other site posted pretty much daily except for Shabbos which I thought was a good indication that the poster is Frum despite the screen name. I waited patiently for the next Yom Tov to see if this poster happened to be away for Saturdays or was actually observant. When the next Yom Tov came and my 鈥渇riend鈥 didn鈥檛 post I suspected the latter.

    I wanted to share my findings with other CR posters but those that I outed denied being who they were and Moderator-80 was very clever and making sure we didn鈥檛 leave any personal information so that posters can contact each other.

    The idea that I came up with was to encode a message by using a private key based on some numbers that were used in one thread with an encryption method described in a different thread. I figured that a handful of posters who recalled both of those posts would be able to figure out how to decode the message and contact me on the email address that I set up for this purpose.

    There were a few posters who decoded the message and contacted me but I was only able to verify that 2 of them were the poster they claimed to be.

    Once I was in contact with these other trusted posters I shared my findings and we were above a 99.99% confidence level that these two posters were the same.

    I continued my surveillance on the other site until I hit a payday. A different poster at the site asked for assistance with a question and the solution was easier to explain with a word document than by typing in a response box on a forum. Instead of sending the OP a PM he embedded a Word document (it seems to have been removed since then)- and to my delight he neglected to remove the metadata from the file! I now had his full name and place of employment!

    Now, I can鈥檛 say for sure if 鈥淛oseph鈥 was just one step ahead of me and sent me on a wild goose chase by leaving red herring all over the place but I did get a huge amount of satisfaction. I wouldn鈥檛 know if any of the pictures I came across while searching his name are actually him- so I don鈥檛 know if I ever saw him in person. There was someone who was in Yeshiva at the same time as my brother-in-law with the same name I never pursued if it was the same person or not as I thought it may lead to Lashon Hora.

    馃崼Syag Lchochma

    Wow! Truly fascinating. Did you ever tell him you figured it out?

    Dr. Pepper

    I once posted something cryptic and it got through the moderators but a few milliseconds later Moderator-80 came around, figured out the underlying message and heavily edited it. Over the years I鈥檝e dropped hints in seemingly innocent posts but they either went right over his head, he chose to ignore them, this isn鈥檛 the same Joseph it used to be or I鈥檓 way off.

    Either way- I pretty much spelled the entire thing out over here so let鈥檚 see what happens.

    馃崼Syag Lchochma

    Thanks for indulging me, I have always been obssessed with mysteries. I starting reading thru all your posts, having a blast. I remember the wagon wheels, wondering what they meant and feeling a desire to be a part of the “in” crowd.

    So far I’ve caught the friedman and khan refrences. Am I allowed to say that?

    馃崼Syag Lchochma

    Dr Pepper- i just had a flash of onspiration. After reading that thread so many times over the years it just occurred to me. Could the wagon be a reference to a squeaky wheel?

    Dr. Pepper

    The wagon was part of a caravan of trucks for a movie that was being filmed there. I hope you didn鈥檛 lose sleep over that for all these years.

    Before a movie is filmed signs go up to let people know to plan their parking accordingly so when the signs went up someone gave me a heads up that the 鈥渨agon鈥 was going to be there.

    I had no idea what he was talking about until one Friday I took a detour to check it out. I tried to keep a straight face because I thought if he saw someone smile from ear to ear when they saw the wagon it would give me away. I walked right by as if I didn鈥檛 notice anything. I also pretended not to notice the can of Dr Pepper left by the wagon.

    This is a public forum so you鈥檙e free to quote anything I wrote but if you think it may lead to Lashon Hora please keep it to yourself. Thanks

    馃崼Syag Lchochma

    That is so funny. No, i don’t generally lose sleep, but i find my brain tends to keep the files open indefinitely. I don’t think i thought about it regularly, just when i came across that thread or a reference. As far as Lashon Hora, I don’t think I know enough detail to know what you mean, so no worries.

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