50 First Dates: Sharks and Jellyfish and (a Very Intense) Hike, Oh My!

Date No. 14 had quite a few red flags, but this dater was determined to give it a shot for love.


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!


What I was looking for at the time

Love, romance, “the one.” What else!


How we met

The dating app Hinge. He looked sweet and athletic. In retrospect, a little too athletic.




Where we went

Chinaman’s Hat (Mokoli‘i). Bad idea. 


SEE ALSO: O‘ahu Hike We Like: Mokoli‘i Island


The lowdown

My date and I were wading into the water with snorkels and fins when the little voice in my head, which sounds a lot like the voice of my middle school adviser and health teacher, cleared her throat and spoke up. Ever since middle school, when one of my friends or I have made a risky decision, we joke that our beloved teacher would be so mad at us after everything she taught us about being a safe and smart woman. Swimming a third of a mile to an island with a man you just met doesn’t sound very safe, she scolded. As if on cue, my date smiled and said, “Oh, by the way, this area has been known to breed hammerheads, if that’s something you’re concerned about.” 


That just so happened to be something I was concerned about.


brie larson


But we’d been planning on swimming out, and I didn’t want to turn back just because it looked farther than I expected. I’d been wanting to explore Chinaman’s Hat ever since I moved to O‘ahu a few weeks earlier, anyway. I silently asked my middle school teacher to forgive me and my guardian angels to protect me, then swam the entire way out praying and imagining how upset my parents would be if I died. When we got to the island, I finally exhaled. Then, I realized I didn’t have shoes. 


Still determined to keep the date going, I tried to hike up anyway. He was far more prepared and wore water shoes underneath his snorkeling fins on the way over. As he shot up the trail like Indiana Jones, I lumbered along the path, trying to step as carefully as possible on the hot sand. The hike was steep. When we reached the rope near the peak, every story I’d heard about people falling to their death in Hawai‘i flashed in my mind. I wasn’t about to die just so he’d think I was worth dating. I finally threw in the towel. “Go ahead,” I told him. So he left me there and climbed to the top.




Then, feeling pitiful on the side of the mountain, I saw them: My saviors. My lifelines. My super-athletic friends from work and their two super-athletic kids! “AHOY!” I yelled with a giant wave, forgetting who I was with.


“Do you guys want a ride back to land in our kayaks?” my friends asked when I explained the situation.


My date and I had barely been able to talk yet, so I wanted us to relax for a bit on the island we’d worked so hard to get to and have a conversation. I also felt slightly embarrassed about climbing aboard my co-workers’ ship with a guy I’d met 45 minutes ago. I said no to the ride.


“You sure? There’s a jellyfish warning at the beach.”


jellyfish Finding Nemo


To my date’s credit, he had checked this ahead of time and had already informed me that there was not a jellyfish warning. I waved them off.


Unfortunately, he had been misinformed. I learned this when, on our swim back, a jolt of electricity pricked my finger, jumped to my lip, then shot down my neck. I screamed—I’d never been stung by a jellyfish before! Wading into shore, I felt scared and sad about what a trainwreck the date had been. All I could conclude was that well-loved classic: You live and learn. I had learned that swimming to Chinaman’s Hat was too ambitious for a first date. I also learned a new favorite classic: always listen to the little voice of your middle school health teacher. 


How did it end/where are the now?

No, he did not pee on me. Our second and last date was on land over a nice dinner. He’s probably not taking girls on first dates to Chinaman’s Hat anymore!




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!



Edit ModuleShow Tags
Edit ModuleShow Tags

Send us your first date!

Have a story that’s even bigger, badder or just ugly? Or what about the best first date ever? Copy the template below and email your submission to web@honolulumagazine.com with the subject line “50 First Dates.” All fields must be filled out. The HONOLULU Magazine team will choose which stories to run at our discretion. If your story is chosen, we will call you to verify your information. Contact information is required for verification only and will not be published; blog posts will be anonymous.


Stories must ...

  1. be true and not slanderous

  2. be about a first date

  3. have taken place in Hawai‘i or involve someone from Hawai‘i

  4. be PG-13

  5. be between 250 and 500 words


Story template

  • What I was looking for at the time:

  • How we met:

  • Where we went:

  • The lowdown:

  • How did it end/where are they now?


Contact info

  • Full name:

  • Neighborhood:

  • Email address:

  • Phone number:



Edit Module

Subscribe to Honolulu

Honolulu Magazine July 2020
Edit ModuleShow Tags



The French Connection

dating in hawaii

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


Before Tinder There Were Bars and Clubs to Meet Up, Drink Up and Hook Up


Ocean’s. Liquid’s. Shipley’s. If you know, you know. If you don’t, you probably weren’t gettin’ jiggy with it. 


He’s Just Not That Into You

dating in hawaii

Sometimes it takes 4–5 great dates to friendzone yourself.