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

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Here we go again with the great timeless debate – who should pay for the first date? Is it the guy, the girl, or should the two go dutch? To my limited understanding of relationships, this responsibility is not gender-based but obviously falls on the person who has asked the other out. It seems that even in the 21st century, not everybody gets that.

Wilson asked Karen out on a date after two weeks of conversing online. He knew her from years back, but in an interesting turn of events, they met online once again and clicked instantly. They were both in university at the time.

Karen was excited. She hadn’t eaten out in weeks, and who would say no to free food? Definitely not her. Beyond that, she had a genuine attraction for him.

Wilson called Karen that morning to confirm that she was still interested in the plans, and she was. In fact, it was one of the few things that were keeping her going through her intense Engineering classes.

That morning, Karen waited patiently for Wilson to call her and offer to pick her up. That call never came. Then she thought that maybe he would be sending her an Uber, but that call didn’t come either. She then decided to call him and ask him if he was going to put the date off.

“No, why would I do that?” Wilson said, “I’ll be there in ten minutes, how far are you?” He asked.

Karen knew instantly that she had to find her way on the date. To her, that was the first red flag. But still, she chose to go. She was broke, as she had spent her last few coins on a night out. She was struggling to get to the end of the month when she would get more allowance from her parents.

Wilson and Karen met at a local restaurant in Hurlingham. It was nothing out of Karen’s ordinary flashy lifestyle. She wasn’t impressed.

However, when she saw him he changed her mind and decided to be open-minded. He looked clean, well dressed, and had an eloquent accent. They instantly hit it off. Karen found herself forgetting that she had found her way to the date, which he had asked her out on. All was forgiven until the bill came.

In a regular fashion, the waitress placed the bill on Wilson’s side of the table. They were both carried away by the conversation, so they ignored it for a while. Then, eventually, when the conversation had died down, Wilson picked it and opened it.

As he was about to open his wallet, Karen said a few words that she lived to regret.

“We can split, or I can just pay for it,” she said, expecting him to instantly decline the offer.

“Yeah, okay. No problem,” Wilson said.

Karen sat there for a few seconds waiting for him to say that he was joking, but it never came. So she opened her wallet and removed the last three thousand shillings she had and paid.

The two parted ways, and Karen went home, bitter. She blamed herself, but not entirely. She was the one who asked him if she could pay, and she couldn’t blame him for accepting. Everybody likes to save their coins.

Karen called her friend that evening asking to borrow some money that would push her through to end month. When her friend asked how the date went, she was too embarrassed to explain. She kept it a secret for years.

The next morning Wilson called her again.

“Yesterday was perfect! Can we start arranging for a second date? I miss you already,” he said.

Karen stayed silent for a few seconds. She tried to speak but couldn’t get the words out of her mouth.

“Sure,” she said finally, knowing fully well that as soon as the call was over, she would be deleting his contact.


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

When He Lies To You That He Is Broke, Then You Find Out He Is Treating Himself To Expensive Spa Dates

When He Got Game But He Is Broke

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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