Kenyan Celebrities Share Their Worst Dates And They Are So Hilarious

Rapper C2K, him of the Kidero Grass fame recalls his worst date, while he was still a student in high school.

“It was during holidays and I decided to take my ‘side chick’ for a dinner date at a posh restaurant in Karen. Just as we were beginning to get acquainted, my girlfriend suddenly walked in, in the company of her parents, siblings and aunt for a family dinner. To make matters worse, they opted for the table next to ours. The date was as totally ruined and as it could be, I lost my bargain.”

Timmy T-Dat

“I was in campus, second year, when I met this ‘chick’ who was a fellow student. Despite stern warnings from her parents that I should stay away from her, we fell for each other. One day, I went ahead and asked her out for a date at a nearby restaurant.

Thirty minutes after my arrival, she walked in looking quite disturbed even as she went ahead to hug me. Before we could settle down, her mean-looking father who had come with policemen caught me. I ended up spending a day in the cells before my family finally bailed me out.”


“It took me less than 20 minutes to exit their company in the pretext that I had gotten an emergency call from home. Since then I never got in touch with the guy again. I even changed my phone number.”


Came into the limelight with the song Mi Casa Su Casa, a collabo with Khaligraph Jones, Cashy was out on a special date some years back with a friend in Westlands when suddenly cops stormed in and arrested everyone in the premises.

She says apart from spending a few minutes inside a police van and the station they were forced to part with the money they were to use on the date. She went straight home after that.

Femi One

“We were in this posh restaurant and as we waited for our meal to be served, we were given some sanitising water that my date ended up drinking instead of washing his hands. You can imagine how I felt as everyone witnessed the clumsy moment.”

Vicmass Luodollar


“We met on social media and I asked her out for lunch. That evening, she willingly accompanied me to our house. One thing led to another and before I knew it, the condom suddenly burst during the heat of things. Four days later I discovered I (had) contracted an STI after visiting a hospital with advice from friends.

Efforts to trace the lady were in vain. I have never met her since.”

Tracey Kush

“Even after making an expensive order in a chic hotel I ended up taking care of the entire bill with the cash I had budgeted for making my hair after he made me believe that he forgot his wallet in the house.”

DJ Eynie

“I met this guy on Twitter and we became friends. He asked me on a date but throughout the date he was on his phone, which is rather rude. I excused myself to use the washroom and left. Fifteen minutes later he realised I had taken too long and called me. I told him I had left and I was on my way home. I never spoke to him again.”

Anto NeoSoul


“I was attracted to this girl I had met in college. Unfortunately she was a beautiful girl with an ugly personality. One day, we went for a date at a place near the University of Nairobi and she became so rude to the waiters that I was embarrassed.

She kept cursing and shouting because of the wrong order and even cutlery arrangement. Everyone wondered what I, this celeb in town, was doing with such a bi**h.

Rachel: TVC Presenter

“I met this guy through a friend and we had been talking for two weeks since we first met. He kept asking me if we could meet up for a date so I decided to give it a try. We went to a fine dining restaurant and he came with his cousin and brother for the date which really puzzled me. As we went on he said it was important for them to meet me as well because he wants to marry me and their approval was important.

I couldn’t take it so I excused myself to the ladies and that was the last time he saw me. I freaked out because this is someone I had met once. I was not ready to run away until he said, ‘she is smart enough not to say no.’ Deep down I kept hoping it was a joke but it wasn’t. He was also proud and could use a class if not two on manners.”

Kyki – Rapper

“I’ve had many bad ones but the worst was with this white guy. When we met he was extremely white. He was so pale you could see his veins; he was scary looking, blonde with green eyes and it put me off. When the food came, I was unable to eat. I excused myself to use the washrooms and left.”

DJ Malaika

“I met this Asian guy at the Coast. We started getting acquainted, he asked for my number and from there we started getting to know each other. When we went for a date he was so rude to the waiter, it made me so uncomfortable that I didn’t want to continue. When we left, we went our separate ways and that was it. He tried calling several times but I never answered.”

Vivian: Singer

“We went for an event together with this guy and once we got there it is like he forgot he had come with someone; he was all over talking to people and I got fed up so I confronted him. I approached him and told him off but since it was a function I left after a short while. He tried calling me but I don’t tolerate such behaviour.”

Papa Dennis

He says that he took a girl out on a lunch date only to be embarrassed by the manner in which she ate the food. “She ended up clearing an entire plate of food, and worse still didn’t know how to use a knife and folk.”


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