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

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What’s your biggest fear on a date? Being catfished or being stood up? Well, for me, it’s being asked to pay for a date. I just can’t stand the embarrassment of a man asking me to pay for whatever reason. My mind instantly judges a broke guy so harshly; I can’t imagine being on a date with one. Little did I know this was about to happen to me.

It was a Friday night and I felt a bit bored so I did what I knew best. I got on my phone and scrolled through my WhatsApp chats, replying to the ones I had left to reply over the weekend. Most of them were simply checking up on me and a few asked me out on a date. After weighing my options, I decided to reply to one guy who had persistently asked me out. At least, it meant he was serious about it. We had never met but we had connected on social media.


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“Hey. Yeah, I’m down to meet.” I texted at around 8.30 pm

Almost immediately, I got a response.

“Finally. Are you free tomorrow?”

“What time and where?” I replied back after a while.

“Afternoon. You pick the place.”

I took a quick look at his profile picture to estimate what kind of date he would be comfortable with, cost-wise. He didn’t seem like a cheapskate nor did he look like much of a spendthrift so I settled for a nice but affordable place.

“How about Charlie’s Bistro?” I suggested since I had been dying to try their Philly Cheesesteak after one of my friends recommended it.

“Really? I took you for a Sankara kinda girl. We could go there if you want.” He texted.

Sankara was great but it was also a fancy hotel which meant that I had to wear a fancy dress and heels. As much as I loved that, I had no plans of dressing up that weekend or spending the whole morning doing my hair and nails. After the long week I had at the office, all I wanted was to put my hair in a head wrap, wear some jeans and converse shoes, and have some Philly cheesesteak.

“Charlie’s is great too,” I answered hinting that I wanted to go there.

“Whatever you want. See you tomorrow.”

Just like that, he went offline without offering to pick me or at least telling me whether he’ll send an Uber.

The next day I woke up in high spirits, well rested and ready to make the most out of the day. I went through my messages as usual and replied to the important ones including one from this guy.

“Hi gorgeous. Are you as excited as I am?” his text read followed with a selfie of him lying in bed.

I was most excited to try out the food at Charlie’s Bistro but I still replied and said yes since he looked like a snack in that picture.

We chatted a little longer and he still didn’t say whether he would pick me so I assumed (correctly) that I was getting my own transport to the place. Luckily, my friend was headed to town so we agreed to share an Uber. I got dressed and headed to pick her with the Uber.

“You are looking good. Where are you headed?” she asked as we got onto the highway.

“You know,” I answered and we both laughed.

“Well, he’s lucky to get all that sauce.”

“I don’t know about that. The guy didn’t even ask how I was getting there.”

“That’s weird. How old is he?” she asked

It hit me that I didn’t even know the guy’s age. For all, I knew he could be a university kid. Yes, I said kid because anyone below the age of 25 is a kid to me. The date started looking suspicious but I was already in the car so …

“Bye. Text me when you leave.” She said as she alighted at her destination.

I got to Charlie’s and found the guy waiting for me with a warm, welcoming smile. He even pulled out a chair for me and complimented me.

“Your pictures don’t do you justice.” He said.

I wasn’t sure if that was a compliment but I took it as such. He looked just like his pictures; handsome and well-dressed. However, my friend’s comment about his age bothered me and seeing him in person I was even more curious. He looked younger than I thought.

He didn’t seem restrained when ordering for food which made me comfortable that he could cover the bill. Besides, the food wasn’t expensive at all. I enjoyed my Philly Cheesesteak but the company was dreadful. Apart from him asking me what I like to do every 10 minutes, he only talked about how he’s trying to start a business. For once in history, someone was relieved to see the bill.

After staring at the bill for 20 minutes, I figured this guy wasn’t going to pay so I picked it up and checked then put it back down. He then did the same but he looked shocked.

“Four thousand, eh.” He mumbled but I heard.

He then asked for the playbill number and pretended that his phone had hung. After wasting a whole 30 minutes, I knew the guy wasn’t going to pay so I removed my wallet. A part of me really wanted to pay my own bill and leave but now that I knew he was a broke guy I didn’t think I could stand the embarrassment of explaining to the waiter that I was paying just for myself.


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As I paid, he sat there meekly avoiding any eye contact with me. I got my change, tipped the waiter since I had enjoyed the food and service, then I got up to leave. He got up with me but I asked him not to follow me or contact me again. How embarrassing!

Moral of the story is, if he asks you to pick the restaurant on your first date, it’s probably a setup. I will never ever go on a date with a guy I haven’t met in person before. I will save myself from embarrassment and also save me some money.

What’s your dating horror story?


The Singlehood Series: When He Got Game But He Is Broke

The Singlehood Series: When He Asks You Out On A Date And Lets You Pay The Full Bill

The Singlehood Series: Ghosted After The Perfect Blind Date

Single Lady In Nairobi: When You Find Out Your Man Is A Gigolo

One Night Of Pleasure, Years Of Regret And Secrets Part 1

The Singlehood Series: The Time Mr. Nice Guy Turned Into A Stalker

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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