The Singlehood Series: My Friends Found Out I Was Dating An Older Woman

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It was never my intention to date an older woman but times were tough and the opportunity presented itself. One of my friends had invited me for a luncheon that was happening at an affluent estate. So, I happily accepted the invite knowing I would grow my network there. When I got there, I felt right at home. The place was full of young entrepreneurs just like me trying to woo potential investors for their latest start-up ideas. I grabbed a drink and walked around the place, trying to identify someone I could approach.

While I was doing my rounds, a woman dripped in gold jewellery caught my attention. She was hard to miss. In case you missed her conspicuous accessories, her loud laughter would definitely make you look. Everyone seemed to enjoy her company so I decided to join her table. She was the only one speaking. Even in the company of fellow powerful men, she seemed to command the room. Slowly, people started leaving to get a drink or bites and before I knew it, I was the only one left with her.

“Young man, you haven’t said a word. Aren’t you here to look for investors?” she said.

“Of course, I am. But I’m more of a listener than a talker.”

“Oh, nice. We would get along very well.”

We didn’t speak about my business or anything related to work. Instead, she told me about her latest trip to South Africa. She was well-travelled and very hard-working which I admired about her. It surprised me how much I enjoyed her company and our conversation. We ended up talking for the rest of the night and she offered to drop me off. Of course, I accepted.

“Mike, I’m leaving.” I alerted the friend who had invited me.

“Okay. Have you called an Uber?”

“Yea,” I replied quickly then left before he could ask any more questions.

Tina was waiting for me in her sleek German machine. The music was blasting loud and she was swaying her head while singing along. Once she noticed me, she unlocked the doors and I settled in the front passenger seat. I tried not to seem excited to be in such a luxurious car but it was hard to hide it.

She asked, “What music do you want to listen to?”

“This is fine. I like local.”

That was a lie but I was too impressed to care. She continued where we had left off on her travel stories. during the entire drive, I kept thinking how much fun her life was. Just as we approached my apartment, she dropped a not-so-subtle hint that she was interested in me.

“Maybe I’ll take you with me on my next trip.”

I was speechless. If I was drinking something, I probably would have choked. She had been flirty all day but I simply thought she was being friendly.

“Sounds great. This is my place. Thanks for the ride. Have a good night.” I said rushing out of the car.

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I looked back and I could see her smirking. At least, that was the last time I would see her or so I thought. A few days passed without any incident. My struggle to make ends meet was getting worse. Then, I got a call from an unknown number. I didn’t have the luxury to ignore calls so I picked it up.

“Hello?” I answered.

“Hi, Kim. This is Tina from the luncheon on Saturday.” She said in a cheerful voice.

Honestly, I was a bit relieved that she had called. Maybe I could make a pitch for my business.

“This is a pleasant surprise.” I perked up.

“Really? How are you doing?”

“To be honest, not very well.”

She told me not to worry – that she would see how to help me. She came to pick me up for lunch. Who was I to refuse when I hadn’t eaten a decent meal in 2 days? It didn’t take long before she called me to alert me that she was outside my apartment. I grabbed my keys and made my way to the parking lot. She was standing outside her car talking on her phone. Again, her loud laughter was hard to miss. I stood a distance away and waited for her to finish the call.

“Get in,” she said unlocking the doors.

“Nice to meet you again,” I said reaching my hand out for a handshake but she pulled me in and gave me a hug.

I gave up. The idea of being a toyboy to this older woman didn’t seem so bad. She wasn’t so unattractive and I really needed the money. So, I flirted back.

“You look lovely today. New hair?”

“Yea. I change my hair every few days.”

Her hairline was receding probably because of the wigs and of course, her age. But at that moment, she looked like a supermodel. Our lunch was brief as she suggested we go to a more private place – her house.

This became a regular thing to a point that my friends started getting suspicious. They would see me get into a fancy car and disappear for days only to come back with hefty shopping bags. It didn’t take long for them to connect the dots and find out that I was dating an older woman. Of course, I never heard the end of it.

“Kim, life is that hard?” One of them said chuckling.

“What do you mean?”

“We know who’s financing your lifestyle nowadays. Don’t think we haven’t seen the woman who comes to pick you.”

“It’s business.”

“Of course it is. Hook us up. We also want designer shoes and someone to pay our rent.”

The jokes were funny at first but they only made me feel more uncomfortable whenever I met with Tina. Eventually, I decided to end things but she wasn’t that willing to let it go. She harassed me at my apartment and called me endlessly. I had to move in with a friend temporarily and change my number until she gave up. Let’s just say, my life may have been a bit easier but I’m not dating another older woman any time soon.

Similar stories in The Singlehood Series:

She Broke Up With Me Because Of A Sponsor

The Dating Trials And Tribulations Of A Cougar

Twitter Boys Looking For Love In The DMs

When You Find Out Your Man Is A Gigolo

When You Realize He Was Just Using You As His ATM

She Found Out That The Other Woman Was Funding Their Relationship

I Had Three Crazy Tinder Experiences Which Forced Me To Delete The App

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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