Sometimes failure doesn’t arrive with a whisper—it kicks down the door, shatters your prized glass figurines, and leaves muddy footprints on your carpet. That’s exactly how my first big failure felt—messy, loud, and a little too proud of itself. Funny thing is, I didn’t immediately recognize it as failure. At first, it just looked like…romantic optimism.

When Jazz Met a Love Story (and the Love Story Hit a Sour Note)

Picture this: I’m 20 years old, fresh back from a semester in Paris, sipping espresso like I’m Godard reincarnated and feeling myself in every possible way. I had just read Baldwin in a Left Bank café! Shook hands with my inner artist! So, when I met Tanya at a friend’s poetry reading in Bronzeville, I wasn’t just confident—I was unbearable. Tanya was stunning—one of those people whose laugh could bend the air around her. She listened to Coltrane, made banana bread from scratch, and was finishing a sociology degree at UIC. She was Chicago, through and through: bold, complex, and a little guarded. In my over-caffeinated, overinflated mind, I convinced myself we were destined for some great, jazz-scored love story.

But destiny, as it turns out, does not care how many Angela Davis books you’ve read or how much French you sling mid-conversation.

The Big Idea That Fizzled

After a couple of magical “we’re finishing each other’s sentences” dates, I decided to surprise her with what I thought was the ultimate third-date gesture: a curated playlist of my heart, burned onto a CD. For the youngins reading this, CDs were like Spotify playlists you could hold in your hand—technology was wild in 2008. I spent hours picking the tracks: some Donny Hathaway, a little Chaka, a dash of Miles to round things out.

Then came the pièce de résistance: I wrote a spoken-word poem to go along with it. Not just any poem—a borderline Shakespearean ode that I recorded and slipped between “‘Round Midnight” and “A Song for You.” The poem, which I titled (cringe incoming) For Tanya, With a ‘Y’, was about our potential. It was about the promise of us, the way her laugh felt like a well-worn hoodie I wanted to wear every day. Heavy-handed? Absolutely. But I was smitten. I saw no red flags.

So, imagine my confusion when Tanya called me the day after I gave her the CD and said, “You’re a great guy, but I think you’re doing…a lot.”

A lot? A LOT?! My fingers hovered over my Nokia flip phone, genuinely unsure how to process her statement. My jazz-infused fantasy was cracking, and I couldn’t figure out why. Wasn’t this what people wanted? Grand gestures! Romance! Donny Hathaway!

The Difference Between Meaning Well and Doing Well

Here’s the thing no one tells you when you’re deep in the throes of doing too much: Sometimes it’s not about how great your intentions are. It’s about reading the room (and not just reciting poetry in it). Looking back, my failure wasn’t in liking Tanya. It was in barreling down a one-way street when she was clearly cruising at a slower speed. Tanya liked me, but she wasn’t asking for “mixtape-eulogizing-our-future-relationship” levels of effort. This wasn’t Love Jones. And I wasn’t Darius.

I obsessed over it for weeks until my mom, always one to keep it real, asked, “Baby, did she ASK for a soundtrack to her life?” The answer, obviously, was no. I had created a love story in my head and auditioned her for the lead role without asking if she even wanted to show up to casting day.

Lessons from the Sultry Wreckage

In hindsight, this “failure” taught me something foundational about relationships—and life. You can’t love people into seeing a future with you. And no amount of perfectly selected jazz tracks will make someone ready for something they’re not. Here’s what I learned that I still carry with me (even when I’m tempted to quote Baldwin mid-date):

  • Check the Pace: Relationships aren’t a 400-meter sprint. They’re more like a walk in the park. If your partner is taking a scenic stroll and you’re running with arms open screaming “LOVE ME,” you’re gonna scare some folks.

  • Know the Difference Between Effort and Pressure: Making an effort feels intentional. Like, “I’m inviting you to a world I want to share.” Pressure feels like, “I built this whole world for you—why don’t you love it?” No one thrives under pressure, except maybe diamonds.

  • Grand Gestures Are Seasoning, Not the Dish: Sprinkle them sparingly once you know the person’s palate. Not everyone likes salt.

  • Let People Be Honest: Tanya told me I was doing too much—and she had every right to. If someone gives you feedback about how they want to be loved, take it with humility. It doesn’t mean you stop being romantic; it means you find ways to express love that feel good for both of you.

Failure Isn’t Fatal, Folks

Tanya and I didn’t work out, and that’s OK. That failure helped me grow. It knocked me off my high horse of “romantic intellectual,” forcing me to embrace something scarier: vulnerability. Real vulnerability isn’t forcing someone to love your quirks. It’s showing up as yourself AND giving them the freedom to do the same.

I won’t lie—it still stung. I listened to “Someday We’ll All Be Free” on repeat for three days straight, but eventually, I emerged from that haze of self-pity. And I haven’t written anyone a mixtape poem since. Not because grand gestures are bad, but because I’ve learned the real magic isn’t in the jazz-filled fantasies we craft. It’s in paying attention, in meeting someone where they are, and in leaving room to build something together.

One last piece of advice? If you’re still out here burning CDs in 2023: Stop. But if you must, maybe leave the spoken-word poetry out of it. Trust me.