I figured this would be a good opportunity to finally talk about Hawaii.
At the end of April, I went to Hawaii on a whim with someone I had met on Tinder and, by the time we left on the trip, had known for 4 months. When he invited me, I had only known him for 8 weeks. As you can probably tell, this story is going to be really short and super boring. I’m sorry, you guys.
When I told my friends that I had agreed to go on this trip, most of my them (understandably) thought I had lost my mind. Many of them feared for my safety—fear that, at the time, seemed silly, but now, looking back, I realize was completely valid. If a friend told me she was going on a two-week vacation to a tropical island with someone she had known for 8 weeks, I’d… well, I’d tell her to go for it. I’m probably not the best person to listen to in this kind of scenario.
I do random shit like this all the time. I have:
Do you understand my vibe now?
When I met Bryan, I was living in Asheville. We matched on Tinder while I had the bio “Pros: Loves anal. Cons: Also loves Chipotle.” He opened with a joke about us getting Indian food. Soon afterwards, I gave him my phone number.
During our initial text conversation, Bryan asked me a lot of questions. Even though I was a snippy bitch to him (a few days earlier, I had gone on a date with someone who didn’t respect my lack of consent—thankfully no physical harm was done to me—and was still rattled), I really enjoyed answering his thoughtful questions because so many men don’t ask me anything. That seems absurd, but I can’t tell you how many dating interactions I’ve had where men haven’t asked me a single question.
After a while, I figured it was my turn. I have no idea why this was the first question out of my mouth—and it’s a question I’ve never asked another person before either—but I opened with: “What is the craziest thing you’ve done recently?”
Bryan’s answer was: “I just moved into a warehouse.”
My response was: “What the fuck did you just say”
As a debatably homeless man, that’s how Bryan’s nickname was born. I started calling him HB, which stands for Homeless Bryan. I asked him for a picture of his “bedroom,” and after receiving it, said, “I’m sorry, but I can’t do this. I can’t get fucked on that table saw. Take care.” His response to my rejection was so kind, he was SO CUTE, and one of my friends was like, “Yeah right, Dana. You can get fucked on that table saw and you know it,” so I caved. After our first date, which concluded when the restaurant had turned its music off and was packing up chairs, we spent the next two days together.
I spent most of those two days giving him shit about living in a WAREHOUSE WITH NO HEAT IN ANOTHER STATE (he didn’t even live in Asheville!). After we parted ways, even though I had given him my usual spiel as I say goodbye to a hookup (which is “if I hear from you again, cool, if I never hear from you again, also cool”), he texted me something disgustingly nice. We kept in touch.
One day, I was walking home from Biscuit Head in Asheville and stopped dead in my tracks. I realized I didn’t have a permanent address and wouldn’t for the rest of the year… which meant I was debatably homeless, too. I texted him this and he laughed.
One thing you need to know about HB is that he’s a total mess of a human. He’s a walking tornado, if that tornado loved nerd shit and the most boring podcasts on the planet. Bryan does the most inexplicably dumb things like buy all 4 versions of Breyer’s vanilla ice cream (Creamy Vanilla, Homestyle Vanilla, Homemade Vanilla, Natural Vanilla—see? I hate that I fucking know this now) and conduct a taste test by himself for no reason, take a 5-hour ADHD test just because he “loves testing and shit,” and invest in bitcoin. He is so dumb, in fact, he invited me on an 11-day trip to Hawaii with approximately ZERO game plan that we had to arrange over the course of less than 2 months. One day in February, completely out of nowhere (no context, nothing), I got this text:
And I’m the stupid, impulsive, unstable weirdo who said yes. Well, my actual initial response to that text was, “Ok but only if you promise me I’ll get lei’d.”
Based on the previous list of stuff I’ve done, while most of my friends were horrified that I was going on this trip with someone I barely knew, my mother just looked at me, sighed, and said, “Of course you are.”
Before we started planning, we set some ground rules:
While we had nearly identical travel philosophies, I also wasn’t stupid. I said I wasn’t buying my plane ticket until he bought his. A few days after the invite, also out of nowhere, I received a screenshot of Bryan’s plane ticket. Well, it wasn’t a screenshot—it was a picture of his laptop with the ticket confirmation pulled up on it that he had taken with his phone. (Did I mention that Bryan’s a dad?) Approximately twelve seconds later, I bought my ticket and sent him an actual screenshot of it like the millennial that I am.
After exchanging travel confirmations, we realized we were on the same flight from Seattle to Kona.
“Make sure our seats are next to each other!” HB texted me.
“Ugh. I have to sit next to you for 6 hours?” I texted back. “No shit I’m going to make sure we’re seated next to each other, I just signed up for 11 days with your dumb ass.”
The tickets were booked. We were officially going to Hawaii, even if at this point we had no idea where the fuck we were going to stay and had seven weeks to figure it out.
The planning ended up being surprisingly easy—all the places we wanted to stay miraculously had availability during the days we wanted. In the end, we decided upon 4 days at an oceanfront house in Pahoa (east side of the island where there are very, very few tourists), 5 days at a farmhouse in Kona (west side of the island), and our final night would be at The Four Seasons just as I had demanded. :)
About a month after we finalized accommodations, I flew from Austin (where I was living at the time) to Seattle, where we’d meet to catch our flight to Kona. We took a selfie and I sent it to the friends who said HB was planning on murdering me and dumping my body into a volcano.
The flight passed by quickly as HB and I shot the shit for hours like we always do. By the time we landed (around 9pm local time), poor HB had been up for nearly 24 hours (because he had flown from the East Coast while I had stayed in Seattle for a few days beforehand and wasn’t jetlagged at all). There was no way his punch-drunk ass was driving to Pahoa. When we picked up the rental car, I had the following conversation with the Avis representative:
Avis: “Are you his wife?”
Avis: “There’s an extra charge of $30 a day for you to drive the vehicle then.”
Me: “Oh hey, guess what? Funny story—we’re married now.”
Avis: "Here are your keys."
And so I drove the 2 hours across the entire island in the dark… in the rain… while stuck behind some IDIOT who was driving ten miles under the 30mph speed limit and BRAKING as we went up a giant hill. HB and I were so tired and dead, we absolutely lost it laughing. We got to our house in Pahoa and collapsed.
When we woke up the next morning, we finally saw our house in the daylight and were dumbstruck. It had two balconies—one downstairs (outside of our bedroom) and one upstairs (outside of the living room/kitchen)—and a pool that all overlooked the ocean. From the balcony, we could see Kehena Beach on the left and one other house in the distance perched on the side of a cliff on the right. That’s it. The rest of it was sapphire blue ocean, palm trees, and rocky shore. It was incredible.
Here is a video because I still can’t get over this house:
For four days, we did as we promised and were complete slugs. We either swam in the pool, went to the naked beach (which was a 5-minute walk away), or relaxed at our house with the incredible views. One night, HB cooked us dinner and discovered he has a pineapple allergy (“My tongue hurts!” - the last thing HB says before he dies) and another night we went to the weekly open-air night market at Uncle Robert’s Awa Bar where we were 2 of the few tourists in a sea of a hundred locals. It's impossible to capture the breadth of the entire market, so here is a small snapshot:
One of my favorite memories will always be lying down on the shore of Kehena Beach, completely naked, and feeling the sun on my face as the waves licked my feet and rolled up to my waist.
Living in Pahoa was one of the most relaxing experiences of my life. There was no schedule. There were no obligations. I was off my phone 90% of the day. The only time I was on my phone was when Bryan and I got horrible idea to troll my friends. And by horrible I mean downright amazing.
Bryan and I decided to get engaged. Five times.
I don’t remember exactly whose idea it was, but I wear a diamond ring on my middle finger that was a gift from my grandmother and, you guessed it, it looks like an engagement ring (though it’s not—Hilda just has mad game). The first time we got engaged, Bryan and I flagged down an older man and his elderly mother (on her birthday!) driving by and asked them to take some photos of us on some lava formations. Then I posted the pictures with the caption “Still in shock. This man is always full of surprises. #engaged”
And then I waited. It wasn’t long before the flood of texts started to come in. I wasn’t sure what to do.
“It’ll be more believable if you go dark,” HB, a literal demon, suggested. He was right. As someone who usually texts back in a timely manner, when I didn’t respond, my friends started to panic. (These texts below are all from friends; I found out later none of my actual family members texted me because they had been sending my mom congratulatory messages, LOLOL.)
I thought that with each subsequent proposal, if I tagged each post on Instagram with the exact same caption every time, surely my friends would catch on. They did not. [“We all believed it because your dramatic ass WOULD make someone propose to you multiple times,” a friend told me afterward. I have never been more offended.]
I don’t know what it says about me that people who’ve known me my entire life would think I would get engaged to a man I had known for 4 months. I don’t want to think about it.
After 4 days of living in absolute paradise, we drove our car across Big Island to our farmhouse in Kona. The house was located on a coffee farm and beyond the rolling hills of tall leafy plants, you could see the ocean. It also had orange trees lining one side of the house and we were told we could pick them and juice them (though we never did because we started each morning with a nice, healthy mudslide). Despite chickens roaming the property and an outdoor shower, the house itself was very chicly decorated and featured a huge kitchen, gigantic bedroom, and tall ceilings. It was beautiful.
“Oh darling, it’s so nice to be back at the country home after four days at the beach house,” HB and I teased each other as we pretended to be wealthy socialites.
The next 5 days went something like this:
The silliness and laughter looked a little something like this:
While we were in Kona, we were no longer slugs. We traveled all over the place. HB wanted to visit some coffee farms and even though I was a less-than-enthused brat, I’m glad he convinced me to go because they were really pretty and fun to walk through.
Here are the beaches we checked out:
1. Hapuna: What I think of when I think of a “typical Hawaiian beach.” Water was super calm and beach was very accessible (some of these beaches require you to walk on some rocky parts for a bit). It's very family-friendly. I don’t have any pictures of the beach by itself because it was a cloudy day, so here is a picture of me beating the shit outta HB:
2. Waialea: Absolutely gorgeous. There are a bunch of fallen and low-hanging trees on the shore, so you can set up camp and essentially make a little carved out, hidden cove for yourself. The water was completely still in some parts and rough in others. I went out and floated in the still parts and never wanted to leave.
3. Kua Bay: This place was insane. It is PERFECT for bodysurfing. The waves were huge, but if you swam out far enough, they wouldn’t crash on you and you could catch a ride on the giant swells. HB even saw a sea turtle swim by us! We also stayed late and watched the sun set and when I sent pictures of it to my brother he texted me, “Are you sending iPhone wallpapers? What the fuck.”
4. Kealakekua Bay: This is the famous snorkeling beach. We admired the candy-colored fish and lace-like coral formations before running into some unexpected visitors.
Though I seem relaxed in this video above, I had experienced a panic attack. There is absolutely nothing creepier than having your head submerged while swimming out into deep waters and hearing the chirps of wild dolphins you can’t see. When we started getting close and I saw a dorsal fin flash by HB’s head, I had visions of his arm being ripped off by dolphin teeth like some Final Destination shit. I stopped and treaded in place, pushed my goggles to my forehead, and told him between gasps—my voice 14 octaves higher than normal—I couldn’t do this. HB swam back over and said we didn’t have to do it if I didn’t want to.
But I didn’t want to be held back by fear. Though I was close to hyperventilating and my stomach was in knots, I was angry at myself for being scared and holding back my own damn self (and HB) from an experience. I said out loud to myself, “No, I’m fucking doing this.” Then HB grabbed my hand and we swam over together.
During the first few moments of our nose-to-nose (or I guess I should say nose-to-snout) encounter, I squeezed HB’s hand so hard I felt like I was going to snap off his fingers. But once the first dolphin glided by us and I watched it cut through the salty ocean with silent grace, it sunk in. We were actually swimming with dolphins out in the wild. So close that I could almost reach out and touch these creatures. It was absolutely indescribable. Beautiful, really.
I had never done one of those fabricated “swim with the dolphins”-type experiences before solely on principle and I’m glad didn’t. Swimming with wild dolphins, while somewhat dangerous, is... there are no words. To say it's incredible doesn't do it justice. We swam with a pod of about 40 dolphins for close to two hours and when we returned to shore, they had disappeared.
We had some other adventures, too.
When driving into Kona, we saw this sign, immediately looked at each other, and cackled. “Why would somebody brag about that?” HB asked.
But it turned out to be really good! HB even asked the cashier how they made their fries. I guess what I’m trying to say is that everyone should try the 8th best cheeseburger in the US.
We tried some local favorites like Kona Brewing Company (the only thing I remembered us eating was the roasted garlic appetizer, which is the appetizer of my dreams), Broke da Mouf (get the pork! and the purple potatoes that I LOVED and HB hated), and Umeke’s (I don’t eat poke, but the short ribs were incredible).
We also had another interesting dining experience… completely by accident.
Before I left for the trip, I had asked one of my coworkers who had grown up in Hawaii for some restaurant recommendations and one of the places he suggested was Kamuela Provision Company. The place had a fancy menu, it overlooked the ocean, and I was feeling bougie so I asked HB if we could go. We typed the address into the GPS and as we drove up to the place, I felt a dark cloud settle over us. The restaurant was located inside… a Hilton Resort.
HB and I had found ourselves in Wristband Country.
As we walked through the Hilton, we passed middle-aged Midwestern tourists with their khakis and socks/sandals combos. These were fine, upstanding people who came to Hawaii to never leave the resort (that’s not a real travel experience! it’s the reality television version!), not traveling heathens like me and HB. I grabbed HB by the forearm and urgently whispered, “We can’t be here.”
One of the reasons we couldn’t stay was because HB and I love to engage in a rather… for a lack of a better word… unique pastime. We love to fake argue in public. To the point that it becomes a screaming match and we attract stares. I have no idea why it’s so fun.
Some things HB and I have argued about are: whether salsa has any nutritional value, why I wouldn’t miss bananas if they ceased to exist (HB was HORRIFIED by this), if dolphins killed people on a regular basis, why bodysuits are called bodysuits and not catsuits (I DIDN’T NAME THESE GARMENTS, HB), if hotels research their customers before they arrive to see if they need to give them any special treatment, how emotionally unintelligent HB is and why I consider him to be an emotional terrorist, etc etc.
I knew we would get kicked out if we fake argued at this restaurant, so we turned around and hightailed it out of there. I think my sandals were on Hilton property for all of 4 minutes.
When we left the gates of the Hilton, I almost wilted with relief. As we started driving toward our Airbnb, HB asked me to go on Yelp and find us a new place to eat.
And that’s where I discovered Privateer’s Cove.
Here are some actual excerpts from reviews of Privateer’s Cove on Yelp:
“What he wants to do is sing a very bawdy, profane sea chanty. Maybe this is an authentic pirate song? I dunno. But it isn't funny, it is just dirty, liberally featuring the c-word. We aren't entertained, and yes we are slightly offended.”
“You’ll either love it or hate it here.”
“Probably not for everyone.”
I turned to HB. “We’re fucking going here.”
There are a few things you need to know about Privateer’s Cove: first, it is a pirate-themed restaurant next to a laundromat inside a strip mall. The whole restaurant’s schtick is that the waitstaff is rude to you. The food is perfectly prepared and fucking delicious (I had a steak and HB and I shared a creme brulee). While there’s a fully stocked bar behind the counter (“That’s for the staff” – the cook), if you want booze, you have to purchase it from what I can’t imagine is a legal alcohol brewing storefront connected to the restaurant. HB left to get us something and returned with a mason jar of “passionfruit”-flavored vodka (trust me, putting passionfruit in quotes is GENEROUS) after being forced to taste test a bunch of hooch.
“Why on earth did you get this one?” I asked HB after I took a sip and it burned off the top three layers of cells in my esophagus.
“Because it was the most disgusting one and I wanted to fuck with you,” HB replied cheerily.
While the older couple at our communal table was scared shitless, being the vagabond weirdos we are, Bryan and I fit right in at Privateer’s Cove. The waitstaff’s gag may have been to give us shit, but I’m a tough New York bitch and so I gave it right back. We definitely had some old timey guns and swords pulled on us as a result. After all the patrons left and the restaurant was technically closed, HB and I were invited to stick around and sing sea shanties.
You heard me right. Sea shanties. For three hours. Call me romantic, but this one was my favorite:
The best thing about Privateer’s Cove is that they had a printed book of about 100+ sea shanties that Bryan and I had assumed were known pirate hymns. That would make sense, right? Nope. They were all written by the owner. And the staff knows the words to every single one of them.
I don't remember how much I drank that night, but let's just say that I smoked a bummed cigarette for the first time in about 8 years and leave it at that. The whole night, between shouting profanities, HB kept leaning over and whispering, “Hilton. We almost ate at the Hilton.” I was laughing so hard, I was in tears.
The next day, we went from drinking nail polish remover next to a laundromat to checking into The Four Seasons.
The Four Seasons is an excellent place to stay if you are sophisticated, rich, and classy.
I am none of those things, so I decided to troll them, too.
By that time, Bryan had proposed to me four times and had decided it was now my turn. While he may have had me beat on quantity, I was determined to beat him on quality.
One night while we were at our country house, HB, the dumbest man alive, complained that he had a hankering for Chicago deep-dish style pizza and actually called restaurants on the island to see if any of them served it. Earlier in the day, we had been trying to think of a plan of how I would propose to him at The Four Seasons. This was before I had told HB that the only place you can find that kind of pizza was in Chicago.
I was right. The place you could get that kind of pizza was Chicago. And so I overnighted two pizzas from Chicago and asked the most expensive beachside restaurant at The Four Seasons to cook it for us because I was proposing to my “boyfriend.” I may or may not have spent $250 to do this.
They fell for it.
So much so that upon checking in they kindly informed us that we had been given a $600 room upgrade.
That night, I proposed to HB and it was fabulous.
We couldn’t have spent our last night in Hawaii in a better way.
The next morning, I cried… because I didn’t know when I was going to see my friend again.
You spend that much time with a hilarious monster and tell me you’re not going to miss him. G’head.
I actually wrote down a list of the funniest things HB said to me because I didn’t want to forget them:
“I’ve eaten a rotisserie chicken over the sink, happy as a clam.”
“My charm and my looks get me out of so much trouble. Like, if I didn’t have a nose, I’d be in jail.”
“I’m pretty normal.” (This one I scream-laughed at before screeching YOU WERE HOMELESS AND INVITED ME ON A HONEYMOON AFTER KNOWING ME FOR 8 WEEKS)
After HB left (his flight home was before mine), I spent the rest of my time in Hawaii alone. I drank smoothies from my private cabana. I got a spa treatment that included a coconut oil massage, a coconut scrub, and being wrapped in what felt like a warm flour tortilla. I swam in the pristine Four Seasons slice of beach and breathed in some deep breaths of gratitude. I realized what a difference a year makes. Twelve months prior, I had gone through one of the hardest periods of my life. I relied on my network heavily as I tried to navigate absolutely everything around me falling apart. (In fact, me having nowhere to live sparked the creation of this trip.) Now I was at the fucking Four Seasons. I had just spent 11 days in paradise laughing to the point of physical pain. During my remaining 6 hours in Hawaii, I didn’t cry. I was beaming.
When I returned to Austin, I took off all my jewelry to put on my bed stand for the night and noticed there was a grain of black sand from Kehena Beach stuck inside my engagement ring. I tried to dig it out, but it wouldn’t budge. After a few minutes, I stopped trying. I figured carrying around a piece of Hawaii with me wasn’t a bad thing.
Dana Hamilton is a writer from New York City currently traveling across the United States on her own for all of 2018. Passionate about everything having to do with the body, she writes about sex, dating, relationships, body image, and eating disorder recovery. She is a frequent contributor to Playboy and her work has appeared in Cosmopolitan, Marie Claire, Teen Vogue, New York Magazine, Time Out NY, and SELF, among other publications. Before she became a freelance writer, she was an editor at two "Big Five" houses in the book publishing industry. She has also written four books (under a pseudonym) for HarperCollins and is currently working on her fifth novel. She holds a BA in writing and nutrition from New York University.
Passionate about everything having to do with the body, Dana Hamilton writes about sex, dating, relationships, body image, and eating disorder recovery. She is a frequent contributor to Playboy and her work has appeared in Cosmopolitan, Marie Claire, Teen Vogue, New York Magazine, Time Out NY, and SELF, among other publications. After driving (and dating) across the country and back on her own for all of 2018, Dana now splits her time between New York, Boston, and Chicago. Before she became a freelance writer, she was an editor at two "Big Five" houses in the book publishing industry. She has also written four books (under a pseudonym) for HarperCollins and is currently working on her fifth novel. She holds a BA in writing and nutrition from New York University.