24+ Dating Horror Stories and What I Learned

Jenn Leach

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I’ve binged over on two dozen episodes of the podcast show Brooke and Jeffrey: Second Date Update and here’s what I learned.

What’s Second Date Update?

Second Date Update is a podcast that was recommended to me by a family member of mine. It’s totally different than other podcasts that I listen to but from the first episode I was totally hooked.

It’s a show on the radio station 92.5 Hubbard Radio and here is the premise of the show.

People contact the show who have gone on first dates and have been ghosted. They tell their story of their first date and have the radio station called their date back, in hopes of landing a second date.

You may think listening to episode after episode of date stories make it boring but each date is totally different and it will keep you entertained for hours.

While I’ve personally been out of the dating game for nearly 2 decades, I can comfortably say that dating is something that I would not be happy to return to. And listening to these stories affirms my decision even further.

What I didn’t realize about the dating world today is that dating is totally different from dating in the past.

My Dating Experience

I met my husband in the early 2000s.

Facebook had just come out and cell phones didn’t have strong Internet connectivity at that point yet. Text messaging was not a thing unless you had a two way pager.

The thing back then was chat rooms and chatting online was something which I definitely indulged in and had fun doing. In our Yahoo chat room you could pop up five or six chats with different people and that could be your Friday evening.

You would get to know people online romantically or for friendship and it was pretty fun.

Your opening line was “asl” which was short for age/sex/location. And this was the opening line that everybody used to get to know someone really quickly from the start.

Today, dating is about FaceTime and text messaging. People are very comfortable online dating and there are tons of online dating sites out there.

People even join multiple dating sites at once.

And dates are becoming more and more inventive apparently. I might be pretty boring but my typical date night is an evening at home where we either cook dinner together drinking wine or grab our favorite restaurant takeout and sit in for a movie.

If we do go out it’s usually a date that lasts a few hours which involves going to the movies or out to dinner. We might be a boring couple, what can I say.

Listening to the podcast really opened up my eyes to the world of dating today. From dates at coffee shops, to private yachts, to meeting people at a pumpkin patch or Facebook stalking, there are plenty of opportunities to meet and date people apparently.

Why Do Second Dates Not Happen

There can be a ton of different reasons why a second date does not happen.

Sometimes people just don’t mesh well or they don’t get along.

They could also just be too different or have different life goals like someone may want to have kids later while the other person does not want to have children in their life.

Here are some of the crazy reasons dates went wrong from this podcast I listened to.

  • The girl pretended to be married to the guy
  • The guy who ghosted the girl was actually a ghost
  • The guy littered by throwing something out of a moving car
  • The girl had an accident (urine) in the guys car
  • The girl punched the guy in her sleep while they were sleeping together
  • The guy stole the girls car
  • They had their date at a coffee shop where the guys ex-girlfriend worked
  • The guy went on a fake date to get on the show and share his skincare brand
  • The guy would only kiss the girl with his top lip

Ok so you can see how wild some of these reasons are.

Without giving away too much I’m gonna go over each one briefly.

The girl pretended to be married to the guy

The first one was a date where the guy was looking at buying a house and he brought along his date with him. She wanted to help him get the house so she suggested that they pretend to be married since couples have an easier time buying a house then single guys, according to her.

The whole thing just freaked him out.

The guy who ghosted the girl was actually a ghost

This next one was pretty creepy. The girl went to a pumpkin patch with her nephew and a worker there was really nice and helped her pick out and carry the pumpkin to her car.

She didn’t get his phone number and with the help of the show called back the pumpkin patch to find him, only to learn that he had died a few years earlier.

What was even creepier is that the pumpkin patch had received calls like the one from the show before where someone saw the ghost and didn’t know it was a ghost, call me back to get his phone number.

The guy littered by throwing something out of a moving car

On one date a guy was the passenger in the car and the girl was driving. There is a cockroach in her car so he threw it out of the window but she thought that he was throwing trash out of the window and the thought of him littering turned her off.

The girl had an accident (urine) in the guys car

A girl was laughing so hard that she had an accident in the guys car (she urinated). She was mortified but learned later that he didn’t even realize that it happened.

The girl punched the guy in her sleep while they were sleeping together

This date went well and needless to say and they ended up having a sleepover. While they were both sleeping the girl punched the guy in the face and it weirded him out so he ghosted her. They got to talk it out afterward.

The guy stole the girls car

The next morning a guy offered to go get breakfast for the girl so he took her car with her permission to grab breakfast and never came back. I won’t give away too much on this one you have to really listen to the show because it’s crazy.

They had their date at a coffee shop where the guy's ex-girlfriend worked

A typical coffee shop date here except that the guy's ex-girlfriend work there and instead of them leaving, they’ve decided to stay which made his date uncomfortable.

The guy went on a fake date to get on the show and share his skincare brand

A fake date with the intention of promoting the guys skin care brand. It was pretty obvious all throughout the call and it was pretty horrible. You have got to listen to this one.

The guy would only kiss the girl with his top lip

Two virgins who found each other on a virgin-only dating app and she was weirded out because all of he would only kiss her with his top lip.

Final Thoughts

Hopefully I didn’t give away too much of the stories here but don’t worry there are tons and tons more. Check out this podcast if you’d like to get a good laugh and if you’re dating it could be pretty eye-opening for you and open your eyes up more about the dating world too, just like it did for me.

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Millennial entrepreneur and writer bringing you fresh content and ideas about making money, side hustles, personal finance, budgeting, and lifestyle. Connect with me: www.millennialnextdoor.com

Katy, TX
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