50 First Dates: The First 12 Hawai‘i Dating Stories That We Blogged About in 2019

We look back at the crazy, funny, awkward and weird submissions sent in by our readers last year. Stay tuned for the next 38!

50 First Dates anonymously chronicles the fun, romantic, wacky, bizarre and downright awful true experiences of dating in Honolulu. Check back weekly for new first-date stories, where to go to woo a boo, tips on where to meet people and more!


we are woke


Let’s face it: Dating everywhere can be tricky. And for managing editor Katrina Valcourt and digital editorial specialist Katie Kenny here in Hawai‘i, it ain’t no different. After swapping stories in the office and during pau hana sessions with friends who have also spent some time in the Islands being single, it didn’t take long for these two staffers to figure out that they are not alone. From first dates that are sweet, scary and sometimes simply strange, HONOLULU’s newest weekly blog shares your stories of dating here in Hawai‘i. And sometimes the best part of a first date is in what comes next. In 2019 we shared 12 first dates that were submitted by you, our readers, as well as two roundups of short stories about The Terrible Tales of Guys and Girls Who Ghost and The 10 Best and Worst Gifts We’ve Ever Received from Romantic Partners. Stay tuned in 2020 for the next 38 first dates plus a sprinkling of tips, tricks, events and roundups. 


1. “He’d Forgotten His Wallet … and Then Started Eating My Fries”

french connection


Pro tip: Don’t ask someone out to dinner if you don’t have any money.

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2. Sometimes it Takes 4–5 Great Dates to Realize He’s Just Not That Into You

drop dead gorgeous


Drop-dead gorgeous inside and out, he was the perfect date but not the perfect mate.

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3. “My Ex Showed Up and Drunkenly Crashed my Date”

drunk ex crash


Things were going very well until a surprise visitor decided it was time to hug and make amends.

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4. “My Jason Momoa-Looking Date Ghosted Me Twice”

jason momoa


Ghost me once, shame on you; ghost me twice, shame on me.

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5. Fearful of Being Catfished She Never Dreamed Her Date Would Show Up High

you're high


What happens when he’s 30 minutes late, fidgety with pupils as big as the moon?

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6. A Millennial Love Story—Tinder, Tacos and Thank U, Next

taco dreaming


Conversation? Sparkling. Food? Delish. Ambiance? Romantic. Relationship? No way.

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7. Baby Got (a Text) Back



This nameless lady on can thank Sir Mix-A-Lot for her new go-to drink order.

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8. It Happened Every Night

dating in hawaii


This date has all the makings of a rom-com: mistaken identity, a lonely single gal getting swept up by a handsome charmer and a whirlwind montage of daily dates. Did the romance burn hot and quick in a one movie deal? Or is this affair a multiseason series with a happily ever after?

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9. He Was Hanging Out Just to Get His Money Back

money back


This boy turned up everywhere—until it came time to pick up the check.

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10. If You Wanna Be My Lover, You Gotta Date All My Friends

group dates in hawaii


She didn’t know it was a date and showed up thinking it was a casual hangout—which means the squad came, too.

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11. He Asked Her Out for Dinner and Then Refused to Order Food

no food


Met your match on a dating app? READ. THE. BIO.

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12. The Most Boring-Sounding Date Turned Out to Be One of the Best Ever



Her potentially crazy co-worker had the most boring date ideas ever but turned out to be the least boring person she’s ever met.

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Check out HONOLULU Magazine every Friday to read the newest story on 50 First Dates and then send your sweet/sad/stupid/scary/silly first-date story to web@honolulumagazine.com. It’s anonymous so no excuses!