You’ve seen the thumbnail. Maybe it popped up on your TikTok FYP or shuffled into a "cringe compilation" on YouTube during a late-night rabbit hole. It’s a split second of pure, unadulterated social friction involving Tyler, The Creator.
People call it the kiss fail tyler moment.
But honestly? Most of the internet has the context completely backward. In the era of 2026, where every pixel is scrutinized for "clout-chasing" or "cringe," we tend to forget that Tyler Okonma has built an entire career on the border of irony and sincerity.
The most famous "fail" isn't even a fail in the traditional sense. It’s usually a reference to that legendary, awkward encounter with Rihanna at the British Fashion Awards, or the scripted-yet-chaotic energy of his 2021 Call Me If You Get Lost era promo clips.
Let's break down what actually happened and why this "fail" keeps trending years later.
The Rihanna "Curve" Heard 'Round the World
It happened back in late 2019, but the internet simply won't let it die. Tyler was presenting or attending the British Fashion Awards. Rihanna, being the undisputed queen of the room, was there to receive an award.
In the clip, Tyler goes in for what looks like a friendly, perhaps slightly over-eager, air-kiss or lean-in. Rihanna—with the grace of a woman who has dodged a thousand rappers—smoothly pivots.
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She doesn't embarrass him. She doesn't push him. She just... isn't there when his face arrives.
It’s the ultimate lesson in social geometry.
Why does it matter? Because Tyler’s reaction wasn’t one of a crushed ego. He leaned into the awkwardness. That’s the secret sauce of the kiss fail tyler phenomenon. Unlike other celebrities who would scrub the footage from the internet, Tyler’s brand is built on being the "weird kid." When he "fails," he wins.
The "WUSYANAME" Aesthetics and Scripted Cringe
By the time 2021 rolled around, Tyler was actively playing with the "awkward romantic" trope.
Remember the teaser for WUSYANAME? He’s on a bike, he’s talking to a girl, and he’s being incredibly "much." He’s doing the most. Fans started clipping these moments, mixing them with real-life fan interactions where Tyler would shut down people trying to get too close.
There's a specific video often mislabeled as a "kiss fail" where a fan at a concert tries to pull him in for a photo or a hug, and Tyler—ever the advocate for personal space—visibly recoils.
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It’s not a fail on his part. It’s a fail on the fan's part.
"I am not your friend," Tyler famously told fans on X (formerly Twitter) in early 2025. "Say hi and keep it moving so I can finish my walk."
This bluntness is why the kiss fail tyler searches stay high. People are obsessed with the friction between a global superstar and the boundaries of his audience.
Why the Internet is Obsessed With "Fails"
We live for the "second-hand embarrassment" of celebrities. It humanizes them.
When we see a guy like Tyler—who is arguably one of the most creative geniuses of our generation—get "curved" or have a weird interaction, it makes the $150 GOLF le FLEUR* shirts feel a bit more accessible. It’s relatable. Who hasn't misread a high-five or a hug?
The "Side-Eye" Era
In 2024 and 2025, Tyler’s Coachella performances added more fuel to the fire. He’s known for calling the audience "ugly motherf—ers" (lovingly, mostly) and keeping a distance.
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So when a "kiss fail" video goes viral, it’s usually because of one of these three things:
- The Rihanna Incident: The gold standard of celebrity rejection.
- The Fan Boundary: Someone tried to touch him, and he said "no thanks" in the most Tyler way possible.
- The Scripted Bit: A clip from a music video or a Loiter Squad-style sketch that people think is real.
Navigating the Weirdness: A Guide for Fans
If you're looking for the kiss fail tyler video to learn what not to do, here's the reality. Tyler treats his public persona like a performance art piece.
If you see him in person, don't try to recreate a viral "moment." Don't go for the "ironic" hug. Don't ask him why he's in a major city (he hates that).
What you should actually do:
- Respect the Perimeter: Tyler is vocal about his personal space.
- Keep it Brief: A simple "I love the album" goes further than a 5-minute pitch for your SoundCloud.
- Watch the Art, Not the Man: Most of his "fails" are actually just him being a normal human who doesn't want to be touched by strangers.
The "fail" isn't a mark against him; it's a testament to his authenticity. In a world of PR-trained robots, Tyler is willing to look a little bit stupid if it means being himself.
The next time that clip of the kiss fail tyler rolls across your screen, look at his face. He isn't crying. He’s probably laughing internally at how much we’re all going to talk about it the next day.
Actionable Insight: If you're a creator or a fan, the lesson here is simple: lean into your awkwardness. The "fail" only becomes a loss if you try to hide it. Tyler turned a "curve" from Rihanna into a career-long masterclass in being unbothered. Follow his lead and stop worrying about the "cringe"—it's the most human thing you've got.