The Singlehood Series: She Showed Up To Our First Date With Her Ex-Boyfriend

Couple having drinks. Image from

I decided to get back in the dating scene after years of being single so naturally, I was nervous about the first date. However, I was looking forward to meeting Samantha in person after talking to her over the phone for a few weeks. She seemed like a bubbly, fun-loving person which was exactly what I needed after coming from a toxic relationship.

Though I had my reservations about dating someone I met online, Samantha was pretty comfortable to talk to and she wanted a serious relationship as well. We made plans to meet over the weekend and I reserved a table at an upscale restaurant in town. None of my friends knew I was dating again until the day I was to meet Samantha.

“Bro, I’m going on a date with this gorgeous girl,” I told my best friend over the phone.

“Date? Since when? You’ve been single for a long time.”

“Yeah. I met her online and we hit it off. She’s really good vibes.” I explained.

“Just be careful, man. I’ve heard horror stories about online dating.”

“It’s fine. I’m ready for whatever can possibly happen.”

I had no expectations. If she turned out to be a catfish – which she could because she looked unrealistically beautiful in her pictures – I wasn’t going to make a big deal out of it. Besides, we had good chemistry and that’s what really mattered to me at that point. I was well into my 30s and I had no time to waste nitpicking my dates based on their looks.

We did a last-minute confirmation that the date was still on then I started getting ready. She may have been toxic but my ex taught me how to dress up for a date. I wore a crisp white shirt with black pants and black leather shoes. Since I wanted to impress her, I completed the look with a watch my father gifted me when I turned 30 – a black, leather strap Daniel Wellington. I looked good and I felt good about the date. I kept imagining how it would go but I reminded myself not to raise my hopes.

At around 5 p.m., I left the house and headed to Westlands where I was to meet Samantha for an early dinner date. The waitress ushered me in and showed me to my table with a spectacular view of the city. I sat for a minute admiring the view and the ambience in the restaurant before the waitress placed the menu before me.

“Give me an Old Fashioned, please,” I said then perused the food menu trying to look for some dishes I could recommend to her.

As I looked through the menu, I felt a shadow beside me and assumed it was the waitress. Then, another shadow pooped up and it hit me that Samantha had finally arrived. Before I could look up, her sweet scent came at me like a punch and I smiled to myself. I knew right there that I wouldn’t be disappointed by what I saw.

Couple having drinks. Image from

Slowly, I lifted my head and the most beautiful woman I had ever seen was standing above me staring right into my eyes. I stood up and reached for a hug and she embraced me back.

“Hi Kenny.” She said in her sweet voice.

“Hi Sammy. You look incredible.”

“Thank you.”

We both went quiet as I waited for her to explain who the man standing next to her was.

“Oh, this is my ex. He insisted that he wanted to come.” She continued then giggled.

I was confused why anyone would show up to the first date with their ex but I gave her the benefit of the doubt. Besides, I promised myself that I’d be a good sport. I invited her to sit and he grabbed another chair from the next table and joined in.

When the waitress arrived, it was more awkward since I had ordered a couple’s starters. Her ex ended up sharing the dish with her as I sipped my Old Fashioned and tried to think about how I’d make an impression when another man was seated right there.

“So, what will you have for dinner?” I asked

“Oh, Sammy. I heard the steak and mashed potatoes here is to die for.” The ex said.

“Really? I think I’ll have that one.”

“I’ll have that too.”

She didn’t even look at the menu.

“There are more dishes you can choose,” I said.

“No. I want mashed potatoes and steak.”

“Okay. What are you drinking?”

“Can we get a bottle of wine?” she asked smiling.

It was hard to say no to her. She was beautiful and had a way to lock you in with her eyes. I made the order and they went back to chatting and giggling. So far, the first date was more disastrous than I could even imagine. However, I didn’t want to tell my friends because they’d either say “I told you so” or they’d come and cause a scene at the restaurant.

I’m not a dramatic person so I sat back and watched them have the time of their life on my bill. It went on for the entire date until I decided to pay the bill and leave them at the restaurant. Samantha offered to escort me to the parking lot which I accepted half-heartedly.

“Listen, I know it looks bad that I brought my ex to our first date but it was a bet.”

She paused.

“I told him about you and he suggested that we play a prank on you to see what you’d do. Honestly, you did really well. I thought you’d leave or tell him to pay his own bill.”

“Sammy, I liked you and I thought I found someone to have a serious relationship with but you can’t expect me to be attracted to you when you still play silly games like this. I pulled all the strings trying to make a good impression and this is your idea of a first date – showing up with your ex. You know what, I don’t think we can work out after tonight.” I explained.

I kept the events of that day to myself and when my best friend asked how the date went, I simply said she was a catfish. She tried to rekindle things but the stunt she pulled that day really put me off that I couldn’t bring myself to give her another chance. Besides, I wasn’t sure if it was a prank or she really did show up to our first date with her ex.

More stories on The Singlehood Series:

He Introduced Me To His Mother But Nobody Told Me My Boyfriend Had A Girlfriend And A 7-Year-Old Son

I Was Cooking For My Boyfriend During Lockdown And He Was Eating My Food With Another Woman

She Found Out That Her Best Friend Was Dating Her Ex-Boyfriend

She Had Aspirations Of Becoming A High Society Lady After A Casual Hookup But It Ended In Premium Tears

Single Lady In Nairobi: The Date With The One That Didn’t Work Out

How I Got Stuck With The Bill After A Date With A Broke Guy

The Date From Hell And Why I Am Never Ever Using A Dating App Again

Facebook Comments
Previous articleHealth & Fitness: 7 Tips To Help You Start Jogging
Next articleSelf-Care: 6 Tips To Live Your Best Mum Life
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