50 First Dates: “My Ex Showed Up and Drunkenly Crashed my Date”

Date No. 3 in our series was heading in the right direction until a surprise visitor killed the vibe.


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!


drunk guy


What I was looking for at the time

Nothing super serious, but if we clicked, I wouldn’t say no.


How we met

I didn’t really feel like going out but a friend of mine was only in town for a few days and she wanted to go to this party at an apartment in Waikīkī. We hit up the party, met a few guys and then bar hopped with them. I spent the evening talking to one of them, a friend of a friend of a friend of a friend of a friend (#justHawaiithings). At the end of the night, he asked if he could give me his number and seemed surprised that I called him right then and there so he could have mine.


Where we went

Our first official date was supposed to be drinks in Chinatown. He was two hours late. (He got called into an important work meeting late in the day and let me know as soon as he found out, but still, that’s a LONG time to wait. I grumpily killed time with a book at the office.) It wasn’t a great start, but he was charming, handsome, fun and very clearly into me, so I rolled with it.


The lowdown

By the time he finally got downtown I was hangry, so we went to dinner at Lucky Belly. I didn’t want the date to be shorter than the amount of time I waited for him, so we continued the evening at Manifest over some Moscow mules. I had a friend standing by to swoop in and rescue me if needed, but I told her it was going well (he was really cute) and we were going to head to The Study in Waikīkī next, so she could leave. Plus, she was hanging out with my ex-boyfriend. They were still friends and I was cool with that, but he was the last person I wanted to see on my way home from a first date with someone new—talk about awkward.


When my date and I got to The Study, we started to sit a bit closer and flirt a bit more. I thought he might kiss me, but next thing you know, my friend and my ex showed up and drunkenly crashed my date. I hadn’t talked to my ex in weeks since he pissed me off the last time we all hung out (I actually thought he was the one who was mad at me), but he came right up to us and started acting all friendly. He hadn’t been that nice to me in ages, which is how I knew he was drunk. I introduced everyone politely and made small talk while screaming internally. When they left, he even hugged me (he’s not a hugger) and told me to call him later. I had a hard time getting back into the mood after that so my date and I finished our drinks and went home. What a killjoy.


How did it end/where are they now?

Despite the awkward ending to the first date—maybe it showed there was competition?—I continued to see my beau every week for about six months, until he dumped me via text at 6:30 one morning. He said he wasn’t looking for a relationship (then what were the past six months?!). Soon after, I ran into our mutual friend at a bar who told me that my noncommittal dude was there—with his girlfriend, whom he’d started dating just a few months after we broke up. They’re married now. So much for not wanting a relationship.


drunk dancing


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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  1. be true and not slanderous

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  • What I was looking for at the time:

  • How we met:

  • Where we went:

  • The lowdown:

  • How did it end/where are they now?


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Honolulu Magazine April 2020
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