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 זכרונו לברכה 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’s reading these questions off a paper or something, but she said that she forgot the list of questions at home so she’s going by her memory.

    By the time he got to her house he hadn’t 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’t by the Mincha that we usually went to and his brother told me that he was on a date.

    I sent him a text- “So, thinking about the girl you’re 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?”

    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 “I felt that I have to be here for you.”


    “I felt that I have to be here for you.”

    Did they get married?

    🍫Syag Lchochma

    That is really awkward. I hope he didn’t 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.

    🍫Syag Lchochma

    These stories just make me more frightened to send my kids out with “strangers”


    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 ”Baska” so as not to pronounce the Shem Hashem by saying “Basya”. He replies “in that case please call me Keilikaku”.

    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’t 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’ll 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 “cake? I LOVE cake! “They offer him some Pepsi and he says “WOW! PEPSI! My favorite! And so on during the date as well. After the date he gets a call from the shadchan who exclaims “What did you do? He thinks to himself oh boy, I really rubbed them the wrong way. The shadchan continues, “they loved you! The parents and the girl are so excited and looking forward to the next date!

    🍫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 “are you a goth?”
    and she said “yes,
    there is nothing wrong with that!”
    Oh I said that’s fine I will be back at 9
    And disappeared before she could lock me in a coffin!

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