Dating in Oahu

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NOTE: This page is a daughter page of: Dating in Hawaii

The Short Version

This is a long article, so for those with limited time, read my shorter article Dating in Hawaii, which covers the main points quickly.

The Backstory

In November 2020 I moved from San Francisco to Hawaii (Maui and Oahu), quickly falling for the many charms of Hawaii - including an incredible fire community. Over time, however, I realized dating here is more different from other places than I could have ever imagined. In this article I'm going to summarize all the warnings and humorous advice I've either experienced or learned about. This isn't just my own experience, I have a large group of awesome female friends (mostly in their 30s) who would talk at length about their dating adventures and frustrations. More recently, some of the guys I have met weighed in with a male perspective. Fortunately, I've collected enough advice and stories that it should be pretty well anonymized and hopefully useful for newcomers to understand the pitfalls in this game of love, sex and trying not to catch covid or something sexually transmitted during your visit!

Dating in Oahu

I'm going to write this in such a way where every subtitle is - I think - an important aspect of Oahu dating you should know about. Let's start with the biggest one of all.


In most of America, one of the very first questions you'll get asked by total strangers is "what do you do for work?". It's really horrible, because what it really means is: "I'd like to define you based on what you do and also I'd like to know your earning potential and if you'll benefit my life". Hawaii is refreshing, because people here mostly don't care what you do. Instead, they are more likely to define you based on what you do for pleasure. Fellow surfer? Awesome. Fire spinning, hiking, kakaing, something-else-outdoors? Awesome. Video games... oh well why are you in Hawaii then - these islands for outdoor people!

Unfortunately, "what do you do for fun" isn't the first question, the first question is "How long are you here for?". First it seemed like just genuine human interest, like my more preferred question "where are you from", but after long enough you realize the real question is "let me decide if you are here long enough for me to invest energy into you". Maybe that seems harsh, but I'm friends with a lot of wonderful locals who talk about the "Oahu Curse". Even among the "true" locals who were born here, many will leave because these are just small islands with limited job opportunities. If you've only been here for a few months or even a couple of years, people will fear that island fever will hit you and suddenly you'll leave forever. Now I'm all for making wonderful chats with strangers, and I love helping tourists by showing them my wikis and telling them to come to fire dancing or volleyball..... but even in a dating context I've learned to ask "how long are you here for", because I've done more than one online date who never disclosed that she was leaving the next day and probably was just after a free dinner.

I felt a little deceived, but that's the game you play in Hawaii, is to be vague about when you might leave, because you still want people to invest in you. For me, I'm in the awkward middle ground where I don't know how many months I might stay. Originally it was 1 month, and at the time of this article it's been 10 months! I honestly don't know if and when I'll have to leave for work.... I'm honest enough to admit that to friends, but the smarter thing I should be doing is being ridiculously vague. At least I know, in my case, I have some friendships here that I feel will last forever - and nobody really knows when they might float in or out of Hawaii... and when that happens it's valuable to have those deep connections!

Back to the topic of dating though. If you're here for only 3 days and you meet a girl/girl who also says they are here for 3 days - and you fance each other... jackpot! Seriously. For people who've lived decades on the island, they are best matched with someone else who also lives here permanently. Now for me, well I'm here because Google has allowed me to be here, and maybe I can be here permanently, but it doesn't change the fact that I'm in the awkward middle ground where I'm best suited to date people who are neither locals nor tourists.

A Tropical Playground

Small Island - The Same People Again and Again

Locals Move Slowly

Women tend to move slowly.

Be Careful Who You Date

Women tend to move slowly.

Highly Private People

Women tend to move slowly.

High Ratio of Men to Women

Worst in the US for men.

Hawaii gender ratios

Military Presence

Look for short haircuts. Story about douchebags on the beach that left all their garbage.

Cultural Diversity

Largely Asian Population

Focus on the Physical

Swimsuit Uniform

Six pack or go home

Instagram Culture

Surf Culture

Flaky the surf is good

Drug Culture

Hippy flipping.

A Culture of Irresponsible Sex

Hippy flipping.

The Spiritual Community

Acroyoga, fire dancing, slacklining.

Increasing Your Chances in Hawaii

Something Casual: try the backpacker experience

Something Serious: conscript your friends

More About Dating in the United States

Calibrating to the United States (for tourists to understand)

Due to its location, fame and idelic weather, Hawaii attracts people from all over the world. If you're not from the United States, I should probably calibrate you first to understand culture. The US has historically had a culture of high economic opportunity - and the best way to get ahead in life here has always been about presenting yourself as successful. The same arrogance that gets you disliked in more polite countries, is almost essential in the US, because people expect it. When I moved to the US I learned very quickly to be more loud, else I would never have a chance to speak. Softly spoken or modest people do exist in rural pockets here, but in the busy cities you have to be bold to get ahead. You often get measured on what you do, and what car you drive.

To me, that was why Hawaii seemed so appealing. Here was a place where people wouldn't ask you what you do for a living.... they were more interested in what you do for fun. If a surfer meets another surfer, they immediately bond and chat about surfing locations. This to me, resonated a little more with Australian culture, where we are more laid back and less showy. Hawaii is definitely more laid back than other places, but I've found people still are much more showy than other countries like Britain, where big-noting yourself or humble brag is seen as pretty low.

Mainland Dating and the Value of Honesty

I can't claim to have dated everywhere on the mainland, but I lived two years in San Diego, many years in San Francisco, and have traveled to 18 states, so that's not bad. Big cities like New York are in some ways amazing to date, because you can sign up to online dating... see thousands of eligible singles and if you can find a way to stand out, then you can meet someone fresh who is either similar to you, or different in very fascinating ways. Most importantly, you can be pretty confident (statistically) that they are not currently dating, formerly dating or roommates with one of your friends. No such luck in Hawaii. In most big cities, the default in the US is non-exclusive.... In other words you should always assume that if you're dating a new girl or guy, that they are also dating one or more other people simultaneously, and if they are too busy to meet you the next day it's probably another person. Other countries this is called "two timing" (slap in the face material), but in the United States, it's just called regular dating. Few people will admit they are dating other people directly to you, but if things do move from intimacy towards deeper connection, then you would have "the talk" about becoming exclusive and then later maybe an official "boyfriend/girlfriend".

When I first got to the US, I learned the slow way that my dates were dating other people. People in most cities are also very flaky - meaning that if you schedule 3 different dates in a week, 2 of them are likely to cancel. This is notoriously true in California where "yes means maybe, maybe means no", and every plan you ever make is "yes, I'll come unless I get a better offer". So if you can't beat them join them right? The difference for me was that I have always been honest to a fault, so I would be very open with any date that I had other dates. But the strangest thing happened. Most girls would appreciate it! I quickly realized why - real honesty is rare in the US, so it really helps you stand out. The other thing that's very easy to do, and makes you stand out as a man. Basic gentleman behavior: pulling out a woman's chair, holding the door, walking on the correct side... these are all so rare in the US you can stand out immediately! Finally: listening deeply and showing an interest in someone else, versus big-noting yourself to try to compete with all the alpha males around you, that makes you stand out as well. Women notice these things.

Unfortunately, you can't not bignote yourself, because nobody can see your personality on an online dating app and you're competing with a bunch of guys that have CEO on their profile. So for me, online dating


Acknowledgements: Some of the fun female friends I've made on Oahu that have told me some of their woes in dating, so that it's not just a male perspective. :)