Flirting is an art, but some people are still painting stick figures when it comes to romance. We asked seven people to share their most awkward, cringe-inducing flirt attempts, and honestly, secondhand embarrassment doesn’t even begin to cover it.

From accidental insults to Wi-Fi passwords doubling as pick-up lines, these stories will have you laughing and wincing at the same time.

Jimmy Fallon

1. The Emoji Overload

by Mojisola

“He sent me a DM that just said, ‘👀🔥🍑😏’—and followed it up with, ‘You get it, right?’”
What I “got” was a permanent ick. The guy later confessed that he thought emojis were a “universal flirting language.” Spoiler: they’re not. My response? The block button—because who wants to decode a Rosetta Stone of cringe?


2. The Karaoke Catastrophe

By Benson

“I was at a karaoke bar and thought it’d be cute to serenade my crush. I picked ‘Endless Love’… and forgot half the lyrics.”
Instead of a sweet duet moment, I awkwardly mumbled through the verses, and she politely clapped when it was over. Later, she told me she “appreciated the effort” but wasn’t into “public embarrassment.” Ouch.


3. The Wi-Fi Password Pick-Up Line

By Cynthia

“He walked up to me at a café, smiled, and asked, ‘Is your name Wi-Fi? Because I’m feeling a connection.’”
I laughed so hard I nearly snorted my latte out of secondhand embarrassment. He was clearly proud of the line, too, because he added, “You can use that one if you want.” Trust me, I won’t.


4. The Accidental Roast

By Timi

“I told my crush, ‘You have the cutest nose… it’s like a baby carrot.’”
Her face went from flattered to offended in two seconds flat. I tried to backtrack, saying I meant it as a compliment, but she wasn’t buying it. Lesson learned: don’t compare body parts to vegetables unless you want things to get real awkward.


5. The Double Text Disaster

By Adams

“I texted, ‘You’re cute’ and immediately panicked because I didn’t get a reply. So, naturally, I followed up with, ‘Or maybe you’re not? Haha.’”
She replied hours later with, “Pick a struggle,” and I haven’t recovered since. Moral of the story? Double texting is like playing Russian roulette with your dignity.


6. The Gym Flop

By Danny

“I tried to impress a girl at the gym by lifting heavier weights than usual. Spoiler: I failed.”
Mid-rep, I dropped the barbell, which landed with a thud loud enough to turn heads. She came over, and for a second, I thought she was going to offer help. Instead, she said, “You okay, Superman?” and walked off.


7. The TikTok Fail

By Perfect

“I made a TikTok professing my feelings for my crush, thinking it’d be romantic. Instead, it went viral for all the wrong reasons.”
People in the comments roasted my editing skills, called the background music “budget Nicholas Sparks,” and someone even said, “Imagine embarrassing yourself like this unprovoked.” The video’s still up—but my self-esteem isn’t.


Conclusion:

Flirting fails are a rite of passage—or at least that’s what we’re telling ourselves to sleep at night. If you’ve ever sent an awkward DM or tripped over your words in front of your crush, just know you’re not alone. And hey, at least you didn’t compare someone’s nose to a baby carrot (probably).


Hey Luv, Wait. Feel More Crackko Vibe:

If you love cringe-worthy fails, you’ll find more in our Ultimate Cringe section.


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