Man covering his forehead with hand

An embarrassing first date story

First dates are a recipe for embarrassing yourself. You’re both nervous. You don’t know each other well.

It’s easy to put your foot in your mouth and say the wrong thing, or fumble with the menu.

I’ve been on a few dates here and there and I can say I am not the most confident person when it comes to date one. It can easily evolve from date one to just one date.

This is a true story because whenever I think about it, I start to simultaneously laugh and cry.

There’s this girl I liked, peng thing, very beautiful and hardworking. I had just left campus and of course, being a young ambitious man, I wanted to show her that I can provide for her.

I was staying at Utawala at that time and so I invited her for lunch at a certain affluent restaurant. I had saved up some money and got to town pretty early as I was very nervous. In my pocket, I had stashed my money and just for good measure added a few hundreds for an ice cream dessert at Uhuru Park.

The lady arrived, looking all sexy. I was saying to myself, what a lucky man I was!

She asked me what I was having and I knew it was her tactic to see how much money I have. So I refused to order and told her, your order. Money-is-no-object. Hehe! She asked for something I have never heard of but I had already scouted the menu, everything was well within my budget, well, unless she orders three plates, which thankfully she did not.

The meal was fantastic and we ordered drinks. As dusk dawned, it was time for the big boy to pay the bill. I had cash. But as I ruffled through my pockets, there was nothing. Have you ever looked for money mpaka you ask your date whether the money is in her bag?

You even go to the toilet to search for the money, yet you never even visited the toilet? I was desperate. Nairobi thugs had fleeced me. How? I don’t even know till today. And the worst part is that these were those days before Fuliza. 

I was new to Nairobi and there was no way my mother would send me money out of nowhere. Ati I left home to go on a date and she had asked me to buy her credit and I told her I have no money? Ha!

When my date realized we were in trouble, and since she also had not come with any money, she panicked. There was no way we could skip town as she was in high heels. I contemplated going to the toilet and disappearing in the wind. At the end of the day, I left my phone and had to go hustle and pay to get my phone back.

I have never gone back to that restaurant again. Oh, and the lady never called me back. I think she lost her phone or something. Lol.

Do you have an embarrassing first date story? Share with us in the comments section. Let’s laugh together!

did you find this useful?

Tell us what you think

LoveMatters Africa

Blush-free facts and stories about love, sex, and relationships