I Catfished My Crush (Kinda) in 1999

💔 Plot Twist: He Didn’t Even Recognize Me

Have you ever put a wild amount of effort into flirting with someone who didn’t know you existed?

I’m talking full rom-com delusion.
Secret identity. Carefully curated charm.
A plan so flawless it practically wrote itself:

Step 1: Woo him online.
Step 2: Reveal I’m the quirky, witty girl he already sorta knows in real life.
Step 3: Kiss before credits roll. Cue epic soundtrack.

It was perfect.
Except for one thing: He only liked me as a friend.

And when the truth came out…
Let’s just say it didn’t end with a grand romantic gesture.

This newsletter includes:

• ✨ A tip to make your dating profile feel less like a LinkedIn cover letter

• 💻 One absolutely unhinged (but relatable) story from my Yahoo! Personals era

• 📝 A rom-com prompt to spice up your bio

• 😬 And a mortifying anti-meet-cute you might still feel in your soul

✨ Dating Tip: Be Memorable (Without Being a Weirdo)

Most conversations on dating apps die because they’re forgettable.

The best way to stand out? Give both a good question and a real answer. Try this:

What’s something you’ve been really into lately? I’ve been watching vintage cooking shows from the '80s. It’s chaos and butter and I love it.

This gives them something to respond to. It’s personal, weirdly specific, and more fun than “how’s your day going?”

📖 That Time I Catfished My Crush (Sorta)

It started like every great made-for-TV love story:
With a fateful online encounter, a soft-focus plan, and a sprinkle of delusion.

I had a crush on a guy I technically knew in real life—my roommate’s boyfriend’s best friend. But he didn’t really know me. Not in a “Hey, want to grab a drink?” way. More in a “Huh, were you at that party?” kind of way.

So naturally, I messaged him through Yahoo! Personals. (It was 1999.)
Under a pseudonym.
Without mentioning we already knew each other.

In my mind, I was just creating a charming little rom-com setup. A slow burn. A surprise twist. A big reveal!
I’d win him over with my sparkling wit, and then… boom! He’d realize I was her. The quirky, clever girl from real life.

Reader, he did not.

When I saw him in person at the bar the next night, I waited for that spark of realization.
He looked at me.
And kept walking.
Didn’t even register me as someone worth a second glance.

Later, when the truth came out (thanks, college gossip chain), he was ticked off. I was shocked. I mean, was it really lying? Or just… storytelling? A little flirt-forward, mystery-narrative world-building?

Okay fine. It was deceptive. But was it any worse than waiting three hours to reply to a text or using your best friend’s dog in your profile photo? Was I catfishing… or just curating?

Either way, the fantasy crashed and burned faster than a 56k modem on a stormy night.

And there was no grand romantic moment.
No kiss in the rain.
Just the slow, mortifying realization that if Hallmark ever launched a spin-off called HallmAwkward, this would’ve been their highest-rated premiere.

📝 Do You Flirt Like a Rom-Com Character or a Cryptic Teenager?

Real-life crushes bring out the weirdest parts of us.

Suddenly we’re strategically “running into” someone. Or DMing them memes instead of, you know, being normal.

It’s easier to imagine the perfect love story than to risk one awkward moment of honesty.

But maybe it’s time to stop writing the fantasy in your head and just… say something.

Start small—“Hey, you popped into my head the other day—made me smile.”

Or go bigger—“I have a little crush on you. Just putting it out there.”

Worst case? They’re flattered.
Best case? You get to skip the slow burn and jump straight to something real.

💬 So… Who Have You Almost Rom-Com’d?

If you’ve ever:

• Orchestrated a “casual” run-in

• Made a playlist for someone who didn’t know you existed

• Spent way too long rewriting a two-sentence DM…

I see you. I am you.

And if you’ve got a story—cringe, cute, or somewhere in the “oh no” zone—I’d love to hear it. Hit reply and tell me:

What’s the most absurd thing you’ve done for a crush?

And hey, if this gave you a laugh (or the gentle nudge to stop lurking in your crush’s Instagram story views), forward it to a friend who might be stuck in their own romantic subplot.

Rom-coms are fun. But real life? That’s where the good stuff starts.

Blue skies,
Carla