The Love Letter Hustle

The Love Letter Hustle for Explored Experiences Journal Dennis Fall for Her Him

Back in primary school, I discovered the ultimate side hustle: writing love letters. Romantic comedies were my jam, and I had a way with words. This classmate once joked that I could make anyone sound like Shakespeare. That’s when it hit me—there was a market for this.

Valentine’s Day season was peak business. Guys who couldn’t string two sentences together came to me in droves. Ksh 30 per letter, personalized to melt hearts. Add Ksh 20 if you wanted a poem thrown in. By midterm, I was swimming in pocket money.

But then, in class seven, I made a rookie mistake. I got a girlfriend.

She was amazing—funny, smart, and had this smile that made me forget my business entirely. I stopped writing for a while, thinking my days as a “wordsmith-for-hire” were behind me.

Until one fateful day.

Her best friend approached me, pesa mkononi (cash in hand), asking me to write a letter for her crush. Harmless, right? Wrong. I’d accidentally created a love triangle. The letter was so good, her crush assumed it was from my girlfriend. Chaos ensued.

My girlfriend confronted me: “Why does your ‘business’ feel like it’s ruining my friendships?” I had no excuse. I’d gotten too good at my craft.

I tried to fix things with a grand gesture. I wrote her the longest, most heartfelt letter I’d ever penned—no fee, of course. She laughed so hard when she read it that she forgave me on the spot. “You’re ridiculous,” she said. “But I like ridiculous.”

From then on, I retired from the love-letter game. Well, almost. I still wrote one now and then every week—for her.