Funny Shidduch Stories

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    tomim tihye

    Shadchan calls me after I gave a very clear NO: “He’s upset that you won’t give him a third date. You have to give him another chance.”

    Me: “I’m sorry, he’s NOT for me. Besides, I’m about to have a second date with the next guy.”

    Shadchan, seriously: “So just tell this new guy that you decided to reconsider the previous guy.”


    Dr P. wrote “I’m curious 2 know how many of the people these

    stories happened w/ got 2 relive the experience by reading it here!”

    I was wondering the same thing. Actually that’s one of the reasons I cant divulge my most embarassing dating stories.

    1)I don’t want to remind these poor girls.

    2)My stories r uniquely me & I dont wanna reveal my identity.

    3)It might make me seem like a shlemazel.

    (the guy the soup gets poured on!)

    All that know me, know that I have this interesting mazel thing. Let’s leave it at that.(I fear I said too much)

    Oh! so now y’all think u know me? No! I’m not “that” guy!

    (…..or am I?)

    Dr. Pepper

    Not so funny, but I wanted to get this thread back on the radar screen.

    I was sitting with a date and schmoozing when a foreigner came up to us and without our permission took a picture of us together. My date was speechless until I said to her, “You don’t mind appearing in the Asian edition of National Geographic, do you”?

    (Not my wife.)


    I know someone who was dating seriously. Her date let her drive his car since she never really drove on the highway before, and he was going to coach her. All is going well until he tells her ok, now you can switch lanes. So she switched, both of them not seeing the speeding car in the next lane. baruch hashem the other car managed to stopped just in time before smashing into them! Her date reassures her it’s ok, it’s nother fault….The girl was all nervous and shaken up of course, but since they were on the highway, she had to continue driving. They continue driving and this girl, still not yet herself, drove through a red light on a busy intersection! Baruch Hashem once again, they got out of that one without an accident too. After that, she let him take over. Now they’re happily married 🙂 🙂


    that story that was floating around before about the step siblings marrying each other is true. i know who they are and b”h married happily. on one side the mother passed away, the other side was divorced and both had kids in shidduchim and so – it was a shidduch!

    Dr. Pepper

    SJSinNYC knows one of them- check out this post:

    This was in response to a post of mine that got deleted asking how they “happened” to have feelings for each other while cleaning for Pesach.


    This story happened many years ago when I was in yeshiva in EY. One of the Israeli bachurim had met so many girls without getting engaged and he was getting on in age, that he started seeing 2 different girls on one evening! One at 6 o’clock, the other at 9.

    There he was walking with the second one, and who do you think he met? The first one. But it wasn’t as embarrassing as you might think, seeing that ……… she was walking with another date too!

    Dr. Pepper

    Maybe Chofetz Chaim can verify this but I just read that the Chofetz Chaim married his step-sister.


    At age 17 the Chofetz Chaim married his step-sister as Kibud Eim to keep the shalom bayis between his mother and step-father (who pressed for the shidduch with his daughter since it was already clear the Chofetz Chaim was great.)

    The Chofetz Chaim’s second wife lived in flatbush and was only niftar about 10 years ago.

    anon for this


    The Chofetz Chaim’s daughter from his second marriage, Rebbetzin Faige Zaks, was niftar within the past 10 years or so. His second wife died quite a while ago.


    “Anon for this”, are you sure Rebt. Zaks’ mother was niftar so a long while ago?

    anon for this


    I don’t know when she passed away, but I think it must have been some time ago. The Chofetz Chaim was born in 1838, so even if she was 30 years younger she was born in 1868, over 140 years ago. She escaped Europe with the Mirrer Yeshiva and is buried in Queens.

    Rebbetzin Zaks lived in e”y towards the end of her life–I visited her when I was in seminary.


    My great-grandfather was about 40 years older than his second wife (my great-grandmother); the Ribbnitzer Rebbe was about 50 years older than his second wife. So if the CC was 50 years older, and she was born in 1888, she may have lived until over 100 years old.

    anon for this

    When I met Rebbetzin Zaks 20 years ago, her mother had already been niftar over a decade previously.


    My brother’s friend had a really crazy story on his first date. He had just picked the girl up from her house, they were in the car and after driving for about 5 minutes, he started to turn left onto the next street, when all of the sudden he was hit from BOTH sides! For some reason (even though usually he’s a really really good driver!) He didn’t look before turning (and no, he was NOT looking at her… ) and his car got hit on both ends. So of course the police and Hatzala come, and she was totally fine so the police drove her back home, while he had to go to the hospital to get checked out. She goes home, tells everyone why she was home not even 10 minutes after she left. About an hour later He calls the house, asks to speak to her, and asks if she would allow him to pick her up in 10 minutes. After some deliberation she said yes, and the rest is history! They got married! 🙂


    music lover i like that one!!!

    simcha man

    music lover29, your story reminds me of someone who was hit by a car. The driver (an 18 year old “Yeshiva” kid) came running over and offered the victim to drive her to a doctor or to the emergency room. The victim, still in shock and still trying to figure out what actually happened, later said it was good comic relief.


    i know of a orphaned boy (from father)who married a girl with divorced parents. The boys mother and girls father met under the chuppa, fell in love and now are married. must be confusing for the grandkids.


    i know of a orphaned boy (from father)who married a girl with divorced parents. The boys mother and girls father met under the chuppa, fell in love and now are married. must be confusing for the grandkids.

    You’d be surprised at how easily kids adapt to non-standard family situations. My kids have had three grandmothers since they were born and they have never been confused in the least on the issue.

    The Wolf



    No one has ever(!) reported suffering from having too many grandmothers. Of course, that’s no guarantee that the child’s parents are as happy with having more in-laws than the norm….

    Dr. Pepper

    While at the Brooklyn Marriott a couple of years back for the Lakewood Dinner my friend asked one of his single sisters to come with him on a “date” to the lounge to see how many guys will date at the Brooklyn Marriott while the yeshiva is having the dinner there.

    They saw three other couples.


    That’s actually AWFUL. Poor girl!


    i know some one who on the first date the guy put onthe music and the song was “od yishama.” It was the first and last!


    Some guys and girls are just stupid and boorish. A friend of ours (now married for a long time) was set up on a blind date, and when the fellow came to the door and she opened it, he was visibly dismayed that she was not a raving beauty and exclaimed, “Oh, no!”

    (And if anyone reading this is the guy who did that, you really hurt this young woman’s feelings and showed yourself to not be worthy of the wonderful person that she is.) Single guysand girls on this forum, PLEASE keep your negative opinions and reactions to yourself when you are meeting someone. MAybe you are no prize in someone else’s eyes, either. At least show some class and be a pleasant date, even to someone whom you have no intention of dating again.

    Dr. Pepper


    I always tried to go out of my way to make sure that I would not offend anyone that I went out with. (I dreaded the thought of calling them on Erev Yom Kippur to ask for forgiveness.)

    On more than one occasion I agreed to go on a second date with a girl so that she wouldn’t think I was saying no because of her looks.

    However, the first time a shadchan told me that the girl was thin and pretty, and that was clearly not the case, I admit that I was taken aback and I sincerely hope she did not notice. I did take her out on a second date and then said I felt she wasn’t for me.

    After that I was always prepared in case the girl wasn’t as described.

    I sure hope I didn’t hurt the girls feeling but if I did the shadchan is the one responsible.


    MAybe you are no prize in someone else’s eyes, either.

    Where does the maybe come in? If someone would do that, chances are theyre no one most normal people (that would be people who have basic decency) would appreciate being married to.



    heres another one; my sisters friend was on a date and he started telling her all of his problems and how he hated life! poor boy, it was a one and no!

    Dr. Pepper

    This comes from a blog I used to read years ago. I don’t have time to post the whole thing now (maybe later) but here is an excerpt.

    The girl appears to be very obnoxious and basically the only thing the two of them can agree on is that there will not be a second date.

    Guy decides to bring up a factual topic incorrectly hypothesising that she will not be able to find anything to argue on.

    Guy: So, what does your father do?

    Girl: He’s a C.P.A.

    Guy: My fathers’ also a C.P.A.

    Girl: Well my father passed all 4 parts on the first try.

    Guy: My father also did and he also scored a near perfect paper on two of the parts.

    Girl: So why do you feel the need to brag about your fathers accomplishments?


    I read this in a book so don’t know if its true- The boy is in the car with the girl(a very high # date) And the girl is yapping away exactly what kind of stone she wants for her her ring. Big, fancy….The boy drives her to a cemetery and tells her, “Here pick whichever one you want”, and promptly broke off any thoughts of engagement.


    that’s mean! but i guess it got the message across.

    Lakewood Mom

    probably not true!

    Max Well

    Maybe, maybe not. But it would of sure served her right!


    A boy came to pick me up for a date. He walked into the front hallway for a minute to shake my fathers hand. Then i started walking towards the door. Most boys let me walk through the door first or they went first and held the screen door open. Not this one. He walked through the door first not looking behind him and literally let the screen door slam in my face! i turned around to face my parents and they motioned for me to just go even though they knew it was not happening. While I was leaving the house, the boy was already at the car. No, he did not hold the car door open or even apologize for his behavior.

    (As a side note, he took me to a milchig restaurant after knowing i was fleishigs.)

    I was home two hours later and no we did not get married 😉


    yiddeshemama-Thats awful!-the milchig restaurant part (the others could have been from nerves- just trying to be dan lekaf zechus)

    a girl once went out with someone extremely tall-that his car was custom made for him! When they got out of the car she saw their reflection in a store window and it just looked comical. This tall gangly guy with a 5″2 girl. It just wasn’t.

    Dr. Pepper


    Yikes, that was me, you seem to be taking the whole thing the wrong way. 🙂

    Well anyway, it wasn’t really me but it reminded me of a story a girl told me about another guy she went out with. After the date, before he dropped her off, he asked how to get to the nearest Dunkin Donuts. My ex-date explained that she was lactose intolerant (and didn’t eat Cholov Stam anyway- I guess by default) so she asked to be dropped off beforehand. The guy explained that he will get totally lost if she’s not there to show him directions so if she doesn’t want to order anything she’s welcome to just watch him eat.

    The worst part of the whole thing was that she lived in a small OOT community where everyone knew each other and a couple of friends saw her sitting there, with no food in front of her, across from the guy who was eating away.


    In line with several stories on this page already. I can’t vouch for the veracity of the story… it may be apocryphal.

    A boy’s family is asking questions about the background of a potential kallah. They ask all sorts of questions about personal conduct (probably including all the stupid shidduch questions — tablecloths, shoelaces, etc.).

    Eventually, they get around to asking about the grandparents and great-grandparents of the kallah. After a bunch of questions, they finally ask “and the great-grandparents… are they buried together or separately?” (i.e. was the cemetary mixed men and women or not.)

    The person answering the question answers in a measured voice. “They were buried together… naked… in a mass grave in Poland.”

    That ended the questions.

    The Wolf



    who cares if the grandparents are buried together or not? i cant believe people ask such ridiculous questions!


    Ok so this was my first date:

    I’m was 22 and I’m in David’s citadel. I’m nervous, pacing up and down. This older fellow sees me and says “you going on a date?” ha, yes! He starts giving me all this great advice and I’m feeling a little better. I ask how long he’s been married, he says he’s not! Ok now I’m nervous again. finally the girl arrives… i mean 45 minutes late. come oooon, seriously??! I’m rolling with the ball though. so as i shakily introduce myself i follow her up the steps… apparently that’s a no no.. go figure. i spot “THE” table. I lead her to it and we get there. My thinking was, find her a seat and pull it out for her (that was my mistake, you shouldnt do that). Her thinking was slightly different. As i walked behind her to pull out her seat she is looking for her own seat. so i am chasing her around like a chicken now waiting for her to stop. On about the 3rd Hakafah she quickly grabs a seat and sits down like a musical chairs game. Holy cow, I’m sweating. I think i was a light shade of green by the time i sat down.

    We dated for a while…. so it couldn’t have been that bad. And no i didn’t marry her 🙁 stinky ending… sorry!


    Shim, Hilarious!… by the EY frum chivalry is not considered tznius…


    no more good stories?


    Guy notices that girl seems to be wearing a sheitel.

    Girl sees quizzical look and says, “I guess they didn’t tell you I’m divorced.”

    “I guess they didn’t tell you I’m a kohen.”

    Dr. Pepper

    Sequel to

    Some background information first- the shadchan was a family friend who thought that if she’s a nice girl and I’m a nice guy why wouldn’t it work? She meant well, I’ll give her credit for that, but it wasn’t meant to be.

    Anyway, she was looking for someone who was going to learn full time which I said I would love to but in case there comes a time where it’s not practical I’d like to get a job. She asked me to commit to 3 years and refused to “bargain” for anything less. I agreed to commit to 2 years (I was two years away from graduation), and said I would like to learn longer if feasible but I refused to promise.

    Since she was flying to NY for a wedding a few days later the shadchan asked us to set that issue aside for the time being and negotiate after the first date if it’s applicable.

    During the first phone call she accidentally said something really inappropriate about herself and I decided that “it wasn’t going to happen”. (Had she been talking to a close female friend it may have been appropriate, but not to a guy she never met before. I didn’t hold it against her since it was obviously an accident. Luckily we were on the phone so she couldn’t see my facial expression and I was able to laugh at it afterwards, but I was terrified at the thought of her saying something similar in front of my family or friends.)

    As mentioned in the linked post- it was one of those “one up one down” experiences, but I did ask for it.

    Getting to the sequel. My youngest brother is totally different from me and the rest of my brothers and somehow he always knows everything. He doesn’t brag about it or anything, but he just knows everything. I never told anyone who this girl is and as far as I know he didn’t even know I was out on a date since he should have been in yeshiva. On top of that, he even knew the reason why she said no. (My only guess is that he found the shidduch notebook my mother kept with all the information about the names that came up for me and my siblings that were dating at the same time.)

    Fast forward a few years. This brother gets a call from the girls mother- apparently she either forgot about me or just didn’t realize that he’s my brother- and asked him for information about two different guys, I have no idea who they are so let’s call them Reuven and Shimon.

    Now my brother knew that Reuven was dating the callers’ younger daughter (did I mention that he always knows everything somehow?) but decided to play along. So when she asked him to compare Reuven and Shimon, my brother explained that Reuven was “busy”.

    “How busy is he?”, she asked. “Uh, I’ll find out and get back to you” my brother responded. “Oh no, you don’t have to. Do you know who he’s going out with?”, she pressed. “You know what? Let me find out all this information for you and I’ll call you back in an hour or two.”

    “It’s OK”, she responded, “don’t bother finding out”. She then asked my brother to compare and contrast the two guys.

    “Well they are both nice people, but Reuven is an exceptional mench and a solid all around guy. Shimon is also a mench but not as big of a catch as Reuven.”

    “Actually, what I really need to know is who is smarter, you see, all my kids are geniuses and they can really only go out with the smartest people around, otherwise they just can’t relate to them.”

    At this point my brother was thinking of telling her who is brother is and asking why her older daughter told the shadchan that I was too smart for her if her kids “are geniuses and they can really only go out with the smartest people around”, but he’s a good brother and didn’t want to say anything without my permission.

    I granted my brother unrestricted permission for the future. My brother found out (some how) that the mother broke off the shidduch between her daughter and Reuven and took Shimon instead. In a casual conversation with Shimon, not knowing that my brother knew who he was dating, he mentioned that he likes the girl but he’s beginning to suspect that she’s a ditz.

    They ended up getting married and as far as I know, that’s the end of the story.



    Back in the late seventies I took the girl to the Planitarium.

    Now, waddaya think happens when you take a Yeshiva guy, put him in a plush reclining armchair, close the lights and tell him to look at the ‘sky and stars’?

    Till this day, every time my wife has a hard time waking me up, she says she had fair warning how difficult it was gonna be!!

    Yes! I actually fell asleep on the date!


    who cares if the grandparents are buried together or not? i cant believe people ask such ridiculous questions!

    As I said, the story may be apocryphal.

    The Wolf


    Dr pepper – thanks for such amusing entertainment! Leave it up to you to find such stories!

    lamdanwanabee that’s hysterical!!! keep em coming!


    Lamdan- now that’s funny! Especially that you ended up getting married!

    Dr. Pepper

    Post Shidduch story-

    At an Aufrof, Sheva Berachos or whatever (it’s not really important) for a friend a different friend pointed to a guy and told me that he’s married to an old flame of mine.

    (Well actually more like an old atom bomb, but that’s for a different post.)

    So the whole time I’m curious to know if she pointed to me and told her husband “there- that’s the guy who I was telling you about…”.

    After I washed for the meal I went to my seat and guess who was sitting in it?

    Keeping a straight face I said, “So, you’re going to take my seat also?”

    He had no idea what I was talking about but the guy next to me was laughing so hard his kishkis fell out and it got served in the cholent. (I guess it must have been an aufrof or Shabbos Sheva Berachos.)


    ITs funny how people have different POV of a situation….

    I heard a story about a boy and girl on a date…The boy offered to open the car door girl said she can take care of herself… Later in the date the girl said something that i am sure the guy misunderstood. throughout the date there was a lot of confusion … When Both sides called the shadchan they BOTH SAID “Well the date was one long mistake…” Thats what they said…..Well… Three years later they went out again and got married… So the lesson that cat be learned….


    Shidduchem is really yad hashem…

    Have you ever meet a person that no matter what they do things go wrong…

    There was a shidduch where the guy tried to open the door and the door slipped out of his hands, later on the date he spilled water all over…. Well the girl also seemed to do stuff like that… Her heels got stuck in a grating, her contact came out…. Well the end of the story is Its really yad hashem…


    you guys are scaring me! I did not start dating yet, but I can’t bear reading these posts….Who knows if they might happen to me!Hope not:)

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