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Some men have no qualms dating a woman who is financially out of their league.
What does it take for a man earning Sh20,000 per month to message a woman who vacations in Zanzibar, drives a German machine, and casually calls champagne “bubbly?” Courage? Audacity?
Whatever it is, there is a crop of men who have no qualms seducing and dating a woman who is financially out of their league, and the game is fast evolving.
Meet the new-age Kenyan man – part lover, part hustler, full-time evangelist of the soft life. This isn’t just dating. It is performance art with a price tag.
The rider with a dream
Brian Otieno, 28, is a bodaboda rider in Nairobi. But don’t let the dusty jacket fool you. He is a man with a vision, and he is dating a woman whose perfume costs more than his monthly rent.
Raised in Kisumu, he started riding boda bodas when he was 19. “It was either that or selling boiled eggs in Kondele,” he says. At first, the job was about survival. He would charge between Sh200 and Sh600 per trip.
But money was not the only thing that motivated him.
“I once dropped a man in Milimani. He went to a salon and came out with a very well dressed woman,” says Brian. “It hit me, these classy women don’t go out with regular men. What if I became unordinary? Would I be more attractive?”
He came up with a plan instantly. He upgraded his motorbike by installing leather seats, a Bluetooth speaker, and a compartment for carrying luggage. He even rebranded himself.
“Me sio Brayo wa nduthi tu, I’m the urban gentleman of the road.” He says with a broad smile.
One evening in 2019, he had just completed a delivery near Sarit Centre mall when he met a woman in a white, flowing silk dress, gold coloured heels and immaculately manicured nails.
She was standing alone and appeared to be waiting for a taxi.
“Madam, you require a ride?” he asked.
She looked him over, skeptical at first, then raised an eyebrow without a word. Brian, without missing a beat, added.
“I will get you to your destination safely.”
That brief trip from Riverside to Westlands was an induction to a new world.
“She was Melissa, the owner of a thriving spa in Westlands,” says Brian.
Some men have no qualms dating a woman who is financially out of their league.
“She gave me a large tip and a flirtatious smile. Would you mind working for me? I would need you to do some pickups, drop-offs daily.”
He accepted without a second thought and in a split second, his world changed. “I didn’t even know some people employ personal riders.
“I showed up early the next Sunday to drop off Melissa’s new stock from a vendor in Kilimani. I made sure I wore a well ironed shirt, sparkling white sneakers and enough perfume.”
He complimented her sunglasses and later helped her set up the boutique displays. She seemed impressed.
“By telling her nice things, I began winning her trust and affection."
The two forged an intimate relationship and after a few months, Brian fled. He had met a new, moneyed woman.
It has been six years since he first dated a woman above his league, and Brian uses the same script all the time. But the response is not always positive.
“There was this woman from Upper Hill. She had a puncture and asked me to drop her at her office. I tried to woo her on the way and she looked at me and said firmly, “I tip riders, I don’t date them.”
That stung.
In 2021 at a wedding in Kilimani where he had been hired as a driver, he met Lilian, a make-up artist whose customers included celebrities.
The two went for drinks after the wedding and Lilian introduced him to the world of fashion displays, brunches, and rooftop parties.
Now in his fourth year of this experiment, Brian has dated five high maintenance women.
Currently, he is seeing three women – a dentist an online influencer, and “a mystery woman. She is different. She sees past the dust on my boots,” says Brian.
“I’m not dating women, I’m dating progress. These women are living a life I want. Dating them isn’t about romance, it is about exposure.”
Now, Brian is planning to start a luxury bike concierge service. Thanks to the big tips he frequently receives, he has bought a new Mazda Demio.
Gymnast who flips for love
Kevin Mwangi, 35, doesn’t just stretch bodies, he stretches limits. A gymnastics instructor at a high-end Nairobi gym in Kilimani, Kevin is tall, lean and moves rhythmically.
But beneath the perfect physique lies a mind strategically worming through Nairobi’s high society one lunge at a time.
His real break came in 2020, when a client, an events planner with celebrity contacts, introduced him to a luxury fitness brand setting up in Kilimani.
That year, he upgraded to a salary of Sh45,000, with private sessions bringing in another Sh10,000 weekly. He began training influencers, models, and wives of Nairobi’s political class.
“It was during a rooftop boot camp in 2021 that I had my first brush with the high-end dating life. I was helping a woman adjust her form during a plank when we got in a brief conversation.
“If you ever get tired of training people, I could hire you privately for more than fitness,” she told him.
Her name was Stella, an interior designer. The relationship lasted six months during which the couple had gone for yoga retreats out of town and visited countless hotels and fancy vacation homes.
“She bought me my first bottle of Tom Ford. I was using normal bathing soap before that. She paid for my passport and a vacation in South Africa and the rest was history.”
Growing up in Ngong, Kevin’s childhood was not of showbiz standards. He lived in a two-roomed house with his mum and two sisters. He got inspired to try gymnastics after watching Olympic reruns on a black-and-white television at a neighbour’s house.
“I started flipping on old mattresses and broken spring beds. At first, it was just to make the girls at school laugh.”
After secondary school, he worked as a volunteer at Tegla Loroupe Sports Training Centre in Ngong. He later got a sponsorship to join a certificate course in sports science. He worked at a medium-level gym and earned Sh10,000 per month.
In early 2022, Kevin struck a conversation with a lawyer he was training. After weeks of subtle flirting, he finally asked her to join him for sushi after the session.
“She glared at me directly in the eye and said, ‘Kevin, I pay you to train me, period. Know your place.’”
A man and a woman on a date.
He went silent for a month, but he didn’t give up.
“Gymnastics taught me that every fall is just preparation for the next flip,” he says.
Shortly after, he met Clara, who owned an art gallery.
“I played games this time. I gave her space, spoke about art, even visited one of her exhibitions at Circle Art Gallery in Kileleshwa. She eventually invited me to a weekend trip to Naivasha with her friends. We didn’t date, but she taught me something important,” Kevin reflects.
“These women don’t fall in love with muscles, they fall in love with men who make them feel seen.”
Kevin has been with seven high-end women in four years.
“One was a divorced mum who texted me at midnight asking me to meet her for wine and yoga. Another was an influencer who calls me her ‘wellness partner’ when people ask.”
Now, he has four women on his radar, each representing a different lifestyle.
“One is a fashion designer, another runs a PR firm, number three is a radio personality, and the fourth one is a popular Bonds investor. All of them make way more than I do.”
Kevin doesn’t see himself doing this forever.
“I want to open a boutique fitness studio in Loresho. Something that’s all about art and wellness,” he says.
“And I want to do it with someone who believes in my hustle, not just my abs. I’ve learned the psychology, the energy, the rhythm. I now know what wine to order on a date. I’m no longer a beginner,” he says.
A butcher who cuts meat and deals
Patrick Ochieng, 36, is no ordinary butcher. By day, he slices meat in Westlands with surgical precision. But by evening, he sips whisky in Kileleshwa restaurants, talking investments with women who own more handbags than he owns shirts.
He is married, with a wife who believes his success is out of his hard work but in reality, Patrick’s secret weapon is charm, carefully wielded among Nairobi’s high-end women.
His story begun at age 20 at Gikomba Market, where he started as a meat loader, earning Sh300 a day. He rose fast from loader, to butcher, to supplier.
By age 27, he was operating his own stall in Westlands and selling to hotels and home chefs. His monthly earnings shot up to around Sh35,000 depending on orders.
In 2018, Patrick had acquired a new client, a woman in Kileleshwa who was very meticulous in her choice of meat cuts.
“She came in a Mercedes, had heels on,” he laughs. “The first time I met her, I was determined to make her a regular customer.
“She asked if I did deliveries, then ordered top cuts for an all-girls’ party the following day.
When I arrived, the house smelled like sweet lemongrass. When I placed the cooler box on the kitchen countertop, one of the women stuck her head inside and said,
“He looks like he knows his cuts, can he help?’” Patrick recalls.
And there he was, sleeves rolled up, marinating ribs and helping to light the grill.
That night, he was offered a glass of red wine. It was the very first time Patrick felt seen not just as a butcher, but as a man.
“At first, it was about curiosity. I started noticing things – how the women carried themselves, how they spoke about assets, yoga, travelling. I started adapting. I asked subtle questions during deliveries and slipped in clever jokes. I also upgraded my dress code,” he tells Nation Lifestyle.
But not all the women he targeted were receptive.
“There was a lawyer in Lavington. I complimented her perfume and she said, ‘Don’t overstep, you’re a butcher, stick to your job.’”
For weeks, he avoided eye contact with female customers, but one day, a customer in Riverside praised him on how neat his packaging was and wanted to know where he sourced his delivery bags.
A happy couple on holiday.
“I realised that I didn’t need to flirt. I could impress by being good at what I do.”
Patrick upgraded his packaging and printed his name and number on biodegradable meat wrappers. Slowly, the women on his radar began noticing.
“They started inviting me inside, asking for tips on where to source the best cuts of meat. One even asked if I knew where to buy a cow for a private farm.”
In six years, Patrick estimates he’s interacted closely with over a dozen high-end women. Not all of them have been intimate, but he’s won trust, relationships, and even referrals. Patrick insists he is not chasing an affair.
“Those women are intelligent, confident and know what they want. It just feels so good to be around them.”
He sees them as mentors, lifestyle coaches, even advisors.
“While my fellow butchers spend the day arguing about football, those women are discussing Bitcoins and offshore bank accounts. I listen and learn."
Asked how he keeps his marriage alive despite the multiple other relationships, he says, “I respect my home, but I also respect growth. And these women aid my growth emotionally, financially and intellectually."
He already fantasises about establishing a high-end butchery in Karen, with glass walls and mood lighting.
“Others think I’m just a butcher,” he laughs. “But in this city, it is not what you do. It’s how you do it.”
