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

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