Home Dating Real Dating Stories: One Hundred and One Dates

Real Dating Stories

It is widely known that human relationships are puzzling and incomprehensible at times. They have been one of the biggest interrogation marks since the creation of the universe and they will still be. And when it gets to romantic relationships… it becomes even more mysterious. Sigmund Freud, the father of psychoanalysis, died without finding the answer to the following question: “what do women want?” And we, women, wonder something similar about men…

There are as many possible relationship combinations as there are people in this world. And even though important breakthroughs have been made in the field of psychology, it is difficult to establish general rules, or come to standardized conclusions when it comes to understanding people, for we are all unique in our own special way.

So, rather than providing some tips on what to do or not to do on dates, I prefer to share with you some Real time dating stories. I invite you to read them, enjoy them and draw your own conclusions…

* All the characters in these stories are completely fictitious. Any similarity with real people is mere coincidence


The Quiz Guy


A friend of his gave him her phone number. So he decided to call her and ask her out. Scene location: they are having dinner at a nice restaurant. And… ACTION!

I am glad you could make it tonight,” he said.

“Well I am glad to be here too. Thank you for your invitation,” she replied.  

“Thank you for coming. Would you like to order?”

“Sure. It’s a hot summer night, so I would like to have a salad.”

“Good choice. I think I’ll have one too. I am going to order a bottle of white wine. Do you like it?”

“Yes! Sure!”

So after the waiter took their order, he started to find about his partner in a most interesting way…

“So tell me… how are you like are?” he inquired.

“That’s a difficult question to answer,” she uttered.

“Let me ask you a few, Can I?”

“Sure, go ahead!”

“Where do you prefer to go on holidays? To the beach or the mountains?”

“Well, I like both… And you?”

“I like the beach. And what’s your favorite material?”

“Excuse me?”

“Yeah, metal? Wood? Plastic?”

“I don’t think I have an answer for that… What about you?”

“I like metal. Don’t worry! Let me ask you a few more…” he replied confidently.

“Okay…” she replied a little bit puzzled.

“What’s your favorite color?”

“Red,” she said.

“Hum. You’re a passionate woman, then. I like that!”

“Where are you going with this?”

“Trust me; I know what I am doing.”

“If you say so…”

“What part of your body do you like best?”

“Well, my eyes, I guess.”

She was completely confused at that point. It was as if he was going to score the “quiz”.

1 to 5 points: they can be friends?; 6 to 10 points: they can continue dating?

“I agree: you have very beautiful eyes. I think we are in a position to take it to the next level and take our first trip together. Let’s take the car now and go to the beach!”

“Are you serious? I barely know you. I think I’ll take a trip… back to my home now. Thank you for this lovely dinner. It’s been most interesting! Good-bye, now!”

She kissed him on the cheek, took her bag… and went home.



They met through an online dating site. After chatting for a while and exchanging e-mails, he asked her out and she accepted. So he invited her to have dinner at a fancy restaurant.

While eating, he started bragging about his ascending career as an actor and his success. He rambled about all his possession and accomplishments all night long. His monologue went on and on to the point she couldn’t even utter a word. After ordering desserts at that fancy restaurant he finally made a pause and gave her the floor… with the following question:

“I am going to ask for the check. Do you have some money with you by any chance?”

“As a matter of fact, I don’t. I thought it was your treat. That was what you told me.”

“Well…hum… what a pickle…”

“Is everything all right?”

“Do you mind coming with me? My car is parked near here…”

“Sure. What about the check?”

“Just give me a sec…” he mumbled.

So they went out the restaurant and surprise, surprise, the car wasn’t there…Apparently, a tow truck had taken it. Was that true?? Maybe it was… maybe it wasn’t. Maybe he didn’t even have a car…

“I think I’ll need to go and fetch my car. Can you come with me?”

A few minutes later, the waiter came out the restaurant …

Sir, you need to pay the check!”

“I can leave my watch in guarantee…” he said to the waiter.

The waiter asked the manager, who agreed to take his watch as a method of payment.

Just at that moment, she decided to take the bus and go back home after having met an ‘unforgettable’ man…

We Are Family!

happy  couple

She went to a night club with her friends and a guy asked her if she wanted to dance…

“Do you want to dance with me?“ he asked.

“Sure, why not?”

“So what do you do for a liv…?”

“What?? I can’t hear you?? The music is TOO loud!”

“What do you do for a LIVING?”

“I am at college. I am studying to be a doctor,” she replied.

“That is very impressive. You like sciences… ”

“Yes, I do. And you?”

“Well, I like sciences too. I am planning to start …”

“I can’t hear you…listen, I have got to meet with my friends now.”

“Would it be okay if I call you one of these days?”

She writes her phone number on a piece of paper…

“Sure. Here’s my number. Bye!!”


Truth be told, he never called her and life went on. Time went by and, one day, she got a new math student who needed to take an exam in order to be admitted to university. ‘Some pocket money was become handy!!’ she thought. She went to her new student’s house for the first class and…

“Hi! I am your math teacher…wait, I think I know you. Have we met before?” she asked.


“Yesss. We met in a night club a couple of months ago.”


“And you called me ‘cause I gave you my phone number. How did you know I teach mathematics?”

“Actually my mom gave me your phone number. You are the daughter of a cousin of hers.

“Ha…we are family,” she deduced.

“I guess we are.”

Baffled, she uttered the following comment

“I have a friend who is an excellent math teacher. Would you like me to give you her phone number?”

“That would be great,” he replied.

“Here it is. I think I should go now…”

“Yes, I think you should. Bye!!”



Based on this evidence and for the time being, it can be concluded that relationships are unpredictable. In Forrest Gump words, “life is like a box of chocolates. You never know what you are gonna get.” Nevertheless, awkward moments make funny anecdotes…






Profile photo of Laura Kluger
I am an English-Spanish translator and writer. Since I graduated as a translator, I have been building bridges of communication among people from different cultures for the sole purpose of enriching their lives with stories from other parts of the world. Most recently, I have started to feel the need to express my personal viewpoint about life, so I have decided to start walking down the road of professional writing. I am a very curious person so I like to investigate, write, and translate about almost everything. Literature and social sciences are the subjects I like the best.
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5 replies to this post
  1. Thank you all for your comments!! They are all very encouraging!! The second part is coming soon!! Your story is hilarious, Bhaskar!! It could easily be part of this saga…

    We all do foolish things when it comes to romantic relationships… the idea behind this article is to have fun with that and to remember those funny stories with a smile on our faces!!

    Thank you for Reading!!

  2. Impressive post. The scenarios are quite realstic and the dialogues are like the cherries on the top. I especially found the Unforgettable guy one funny, though I guess such guys are somewhat rare. This post reminds me of a funny dating experience of mine. My gf was upset with me for something and to appease her, I had written a soulful letter. I then called her and nervously spoke its contents on phone, only to realise that instead of her, her mom had picked it up. Embarresed, I was left saying sorry.
    Anyway, waiting further posts, keep them coming

  3. ” This is an excellent idea of posting stories instead of tips. Great work. Much help.”

  4. I can so relate to the “Unforgettable” dating story. Guys who keep on blabbering around their success aren’t successful at all. All they know is to brag and make stories.
    But the fact that the girls are always courteous has been brought about very well.
    Good Job.

  5. Entertaining dating stories that will leave you amused..
    If you also have interesting or weird date expressions, Share with us!
    We promise we will post them as anonymous! Just message us…
    The experience that gets the maximum likes will win a surprise gift!!