50 First Dates: Sometimes it Takes 4–5 Great Dates to Realize He’s Just Not That Into You

Or how we realized that great connection was merely platonic. Welcome to date No. 2—one that by all accounts should have ended well.


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!


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

movie date


What I was looking for at the time

Something of substance. I’ve had the one-night stands, friends with benefits and got caught up in expiration dating (a relationship or fling that has an end in sight or no chance at a future)—now in my early 30s I want something with a potential future. I’m not searching for a husband, but a lifetime partner in crime/lover would be ideal.


How we met

We first met on Tinder but after many delightful conversations he addressed me by the wrong name. I immediately categorized him as a f***boy and stopped responding. Six or so months later we matched again on Bumble and started talking again. I think we had both forgotten about the Tinder exchange during the first date. We chatted on the app, he asked for my number and then I mistakenly gave him the wrong digits. I was sad I didn’t hear from him and then he sent me the man-shrugging emoji on Bumble. It was then that I realized my mistake. He texted me within the hour and we set up a date.


Where we went

I gave him three options and he chose the one I really wanted: An outdoor sunset screening of the film Adrift at Ward Village.


The lowdown

I was nervous. I had only seen pictures of him on the dating apps we had matched on and he appeared to be beautiful—way out of my league. We decided to meet at Whole Foods in Kaka‘ako to pick up some nibbles to enjoy during the screening. As soon as we met I was keen. He was smiley, sweet, handsome and well dressed. We awkwardly poked around the self-serve bar to fill up our to-go boxes of food and then headed to the outdoor cinema. Arriving early meant we could discuss our travels, a mutual love for outdoor adventures and what brought us to the Islands. The charmer charmed me. The choice of film seemed to be a perfect match for us and I felt comfortable with him despite only meeting him that night. Afterward, we walked a little and then hugged goodbye. Nowadays, I am not the type to kiss on the first date if I like someone (I get too nervous to make the first move) but I did wish he had made a little move to kiss. I questioned whether or not I flirted enough.


How did it end?

Not going to lie: When he texted, “when can I see you again?” a day or two after, I was excited. We met up multiple times after that for creative and fun dates (a concert at The Republik, dinner at Fête and so on) but we never kissed. After a day of snorkeling around various West Side spots, I texted him asking why it felt like we weren’t progressing. He responded with an honest answer that I fully respected. I suggested we become friends and we have been ever since. Sometimes wonderful people aren’t your soulmates but I am a firm believer that they can still be in our lives in other ways.


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



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!



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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.


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Honolulu Magazine July 2020
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