50 First Dates: The Most Boring-Sounding Date Turned Out to Be One of the Best Ever

Date No. 12 goes to show that just because the activities are dull doesn’t mean the person is.


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!


My potentially crazy co-worker had the most boring date ideas ever but is the least boring person I’ve ever met.


What I was looking for at the time

Nothing! I had just moved to the island and didn’t plan to stay more than a year or two, so I wasn't exactly looking for a soul mate. I also thought this guy might be insane.


weird dog



How we met

We worked together and had hung out a few times, eventually getting very drunk and having some—how should I put this—nighttime escapades, before I agreed to go on actual date with him.


Where we went

To a driving range, a grocery store, Young Lunch Wagon, the beach and then his apartment.


happy gilmore


The lowdown

I thought going to the driving range sounded super boring, but it turned out to be so fun. We were both horrible at it and we laughed at the very professional golfers giving us dirty looks every time we hit the little divider fences. Also, it was obviously an excuse for him to put his arms around me to “show me how to swing” or whatever. We hit grocery store to get alcohol, and a toothbrush for me because there was apparently no pretending we didn’t know where this was heading. Then we grabbed a very average plate lunch from a random food truck in Makiki that we ate on the beach behind the Hilton lagoon, and then we just went to his apartment to get drunk and do other nighttime things.


How did it end/where are they now?

At the time I remember thinking that he was a little crazy, and there was no way this could go anywhere. But while I felt that it was full of subpar date activities, I had the most fun I’d had since moving to the island four months earlier. Two years later, I was right about not staying on the island very long, but wrong about him. We’re still together and I still have the most fun with him, even with 5,000 miles or so between us. Fingers crossed he moves out here to L.A. soon!


SEE ALSO: 50 First Dates: The 10 Best and Worst Gifts We’ve Ever Received​ 

you can do it gif


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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Honolulu Magazine July 2020
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