Q and A #5- Your Dating Stories!!
- Shira
- Mar 6, 2024
- 6 min read
Updated: Mar 8, 2024
Q & A Questions on hot-button topics with Your Answers!Q)

In honor of Adar, please share your funniest/craziest/weirdest dating story:
Your Answers!
One of my many dating stories was.... meeting my sister in the hotel lobby on a date (one part of younger sisters in shidduchim with you.....:))
P.S. We tried arranging not to meet each other beforehand, but both shadchanim weren't able to find out where the boys were going beforehand.... was not funny in the moment, but looking back, it is. -Anonymous
I was sitting on a first date at a hotel—you know, the regular family talk—this sister, that brother, ;)—and then, from the corner of my eye, I saw a mouse—yes, a mouse—fly past.
I thought I must be dreaming, but my confusion was clarified when I saw it scurry by AGAIN!! Oooh lala was I ready to escape. Miraculously, something below me glued me down to my now uncomfortable sofa;) To this day, I wonder if the guy saw it, too, and kept quiet, just like me😉 - C.M.
When the guy backed into the mailbox cuz he was too busy putting the address in his GPS!!! -Anonymous
A few years ago, I went to a carnival with a guy. I believe it was our 5/6th date, and we went on a carnival ride. What we didn't realize, though, was that the ride went in circles, and centripetal force is definitely a thing- whoever is sitting on the outside with be forced inward. I was the one on the outside, and I was being pushed towards the center of the circle. No matter how hard I tried, I could not hold myself back from leaning inward on top of the guy next to me. In the end, we both got off the ride and were laughing hysterically, pointing out the fact that we both totally did not realize what would happen on the ride before we got on. He said to me, "Well, if nothing else, we have a good story to tell our kids and grandkids one day!" and we continued on with the carnival. -TJ
So it was on a first/second date and the boy I was dating asked if I have grandparents who are alive and I burst out crying since my grandfather had just passed away… it was definitely awkward…
We were stuck in a traffic jam for an hour on the way home, and the boy goes, “This date is way too long… “ (like what am I meant to do;)) - Anonymous
Here are some funny ones...
All these happened with the same guy I was dating. On one date, he got pulled over for being unable to stay in the lane. On another, he crashed on the highway. After all the drama with the police and everything, we continued on our way, and he almost crashed again! Then, he drove straight over the curb in the parking lot when we got to the place. On the next date, it was right after a snowstorm, and he drove straight into a massive puddle/pothole and could not get the car out! Finally, he slammed on the gas, and we went flying into the bushes nearby. Then he put the car in reverse to back up and slammed on the gas, so we went FLYING backward. After that rollercoaster, I was DONE. -Anonymous
This story didn't happen to me but to a friend of mine.
The guy came to pick her up for a first date, and when she got into the car, he turned on blasting music and started singing away. Then he turned to her and asked if she would like to sing along!!! Needless to say, it was a one-and-done!
They say dating is a wild ride, but I never realized that this can be literally!
I was on a first date. As the boy drove to the hotel, people who passed by kept flashing their brights to indicate his headlights weren’t on. When this happened, the boy would raise his hand in thanks but not do anything; it was really bizarre, TBH. I figured he had no clue what people wanted from him so I played dumb and said, “Are your lights on? I’m wondering if that's why people are brightening you.” He said, “Oh,” and seemed to turn them on. We were on the highway, but the road still looked really dark. I strongly suspected his lights were still off, but I felt awkward telling him to turn them on again, so I didn’t. We were halfway to the hotel when I suddenly saw flashing lights behind us- a State Trooper- Yee-haw! The boy totally panicked and swerved to the right, almost crashed into the guardrail, and finally made a short stop. The cop got out, slowly walked over to the car, and shone his flashlight in for a long time. I couldn’t see and was terrified. My mind started conjuring crazy scenarios- “The cop prob thinks the boy is drunk because of how he drove. Now we’ll have to take a breathalyzer test, and we’ll be arrested, and this will be aired all over TV, and OMG, this is mortifying. How did I get myself into this mess?” (I’m laughing right now as I write this, but I remember really thinking this and being on the verge of tears at the time).
The cop looked at the boy and asked the usual, “License, registration, and insurance.” The boy took out his license and gave it to the officer, who responded, “I need your insurance and registration.” “One second,” replied the boy. I'm just going to get it out of my pocket.” “You keep it in your pocket?! Who keeps a registration in their pocket?” the cop sneered (I can still hear his voice after all these years). BH, I had my brain in and remembered that rentals keep the registration and insurance card in the glove compartment. I gave it to the cop. “Do you know why I pulled you over?” he asked the boy. “Your lights are off. Can you turn them on for me?” The boy complied-thankfully this time he really did turn them on. The cop returned to his patrol car and came back a few minutes later and said, “I'm not going to give you a ticket; this is just a warning. But make sure you keep your lights on.” I guess he realized we were both very nervous, so he tried to lessen the tension by asking, “Where you guys going?” and I was thinking- “Omg, this is getting more awkward by the second.” “I'm going on a date,” said the boy. “Oh, that's nice! Where are you going?” The boy named the hotel, and the officer smirked and said, “Well, enjoy your date,” and let us go.
Alas, if you think my story is over, it isn’t.
I guess the boy was on edge after that and wasn't concentrating on how he was driving or, rather, WHERE he was driving. We were literally a minute from the hotel. All he had to do was make a left at the corner and then drive down one block to the parking lot. Well, when he came to the corner, instead of turning left, he shot through the stop sign and continued driving straight- straight onto the hotel's lawn!!!! I was like, “Okay, this is retarded!!” I expected him to stop, but he continued driving at high speed on the lawn- I felt like I was in a horror movie… and then I noticed that we were heading straight for the electrical box that supplied the electricity for the whole hotel. And I'm like to myself, “OH MY G-D!! We're literally about to go full force into this thing!” “STOP!!!!!!!” I screamed at the top of my lungs. Suddenly, as if the boy was in a dream, he perked up and said, “What?” and stopped the car. I was so shaken up we were literally inches away from this electrical box. If we had driven a few more inches, it would’ve exploded, and I don't want to say what could’ve happened… He backed onto the street, drove into the hotel’s parking lot, and parked the car. We got out; the bumper had been knocked off three-quarters of the way… We found a place to sit, and I told him I needed the bathroom. As soon as the door shut, I cried my eyes out. All my eye makeup was rolling down my face (even though it was supposedly waterproof). A frum girl who was also on a date walked in; I was standing by the sink crying. She looked a little alarmed, lol, but I couldn't tell her anything. I finally composed myself and told the boy that I was not feeling well (which, at that point, wasn’t a lie) and said I needed to go home earlier than expected. We talked for a bit, but thankfully, he cut the date short. I BH arrived home in one piece. You can be sure that I never went out with him again!! FYI- I now bring my phone with me on dates just in case I get stuck with a wacko and need to call 911 or an Uber;) -Anonymous
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Dating stories like these are pure entertainment 😂 From mice in hotel lobbies to mailbox crashes, it’s almost as unpredictable as finding call girls in Bhikaji Cama Place 😅💥 You never know what twist is coming next! 💃📍