The Singlehood Series: When He Shows Up To Your First Date With A Friend

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The dating scene will teach you a lot of things, and for that reason, Ashley believed, everyone should experience dating multiple men at least at one point in their lives. You get to learn what you like and what you don’t, your negotiables and non-negotiables, and much more.

Ashley thought she had seen it all, but she was proven wrong almost every single time. She was enjoying this dating life, ever since she had been badly heartbroken by her ex-boyfriend.

She met this guy in a matatu. Somehow, she had talked to this particular stranger, something she would not ordinarily do. They exchanged numbers and soon it was time for her to alight and walk to her house.

Shem, the guy, didn’t waste time. By the time Ashley was unlocking the door to her house, he had texted her. It was great meeting you today, hopefully, I can see you again soon? 

Ashley was instantly impressed. In this game of dating, what she hated the most was endless texting and speaking over the phone without ever meeting.

A week later, the two of them were to meet. He had asked her out to a fancy restaurant in Town. She dressed up, put on her makeup and was ready to leave. She had always wanted to try that restaurant and this was the perfect opportunity.

That day, Ashley chose to use an Uber. This was partly because she was late, and partly because she was in pure white and thought that she’d get dirty if she used other public means.

Shem called her. “Hello, where are you now?”

In the background, Ashley could hear some noises, as though he was with someone. But she chose to ignore it.

“I’m almost there. I will be there in ten minutes,” Ashley replied. She was quite impressed that he was there on time, earlier than they had agreed actually. Was this a second green flag? She wondered.

Ashley walked into the restaurant at 12:30 pm. She was gorgeous. When she walked in, all heads turned. The waiters were quick to ask her whether she had a reservation, and where she would like to sit.

She called Shem. “Hello, Shem. I’m here. Please come for me at the entrance.”

When Shem walked over to her, he said something that caught her aback but she chose to ignore it.

“Have you waited too long?” She asked.

“No, actually. We’ve only been here a few minutes,” he answered.

As they walked over to the booth, Ashley confirmed that he had actually said ‘we.’ There was a guy sitting at the table. He had invited his friend on their date!

It was awkward. Ashley didn’t know whether to sit on Shem’s side or his friend’s side. Weirdly enough, once she settled down she actually had a good time.

The food was great and the conversations were flowing! She found herself drawing closer to Shem’s friend. He had a great sense of humour and was easy-going. What a shame! (See what I did there?)

At the end of the date, Shem’s friend, Nick, asked Ashley for her number. She walked out of the restaurant feeling weird, the more she thought about it. Since everything was all up in the air, she decided to ignore both of them and ghost both of them after that. She didn’t want to cause any tension between the two.

That was a great ‘date.’ She had a good time, ate good food, and got to try out a new restaurant. There was only one question that remained on her mind was this – “Why would you invite your friend to a first date with another girl?”

Check out

She Showed Up To Our First Date With Her Ex-Boyfriend

He Went On A Blind Date And Had Dinner With The Wrong Girl

He Asked Me Out On A Brunch Date But Took Me To Church Instead

I Confessed To Stalking Her On The First Date

An Embarrassing Encounter With My Date’s Daughter Left Me With A Bruised Ego

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The singlehood series is a collection of real-life stories and opinions from different people. It looks at the current world of dating in Kenya and experiences that people have gone through. The views and opinions expressed here are those of the contributors and do not necessarily represent or reflect the views of