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.
I know, I know. I post to “Eat, Drive, Fuck” faithfully every week, but that didn’t happen last week. But I have a good reason, I promise.
The first—and biggest—reason I didn’t publish anything last week was that I wrote an AMAZING post that is the longest I’ve ever written for this blog, FULL of pictures and videos that I'm really, really proud of (and it took a lot of time!)… and then had to delay posting it for very exciting reasons. Stay tuned. [There is a separate, HUGE announcement at the very end of this post!]
Next, I drove from Denver to the Grand Canyon (which was just as fabulous as I’d hoped it would be) to Phoenix to LA all in the span of a week.
Then I left my car in LA and caught a red-eye to New York. I had to come home for a specific event for my day job and my father’s surprise 60th birthday party and so I tacked on an extra few weeks to see friends, have a meeting with my agent, and talk to some lovely people I met at the sex therapy and education conference in Denver.
Essentially, I had 21 days to fit in meetings with 347 people. It’s been so fun, but also exhausting. I also think I have a bit of an emotional hangover because this past Friday, I visited my old neighborhood in Queens—my home before starting this trip. It was more emotional than I thought it would be because I thought of how far I’d come (both figuratively and literally since I had lived in NY my entire life) since I left.
As I walked around Astoria, I passed the shitty diner where I’d get bacon, egg, and cheese sandwiches after late nights at hookups’ apartments, the laundromat where I was SO EXCITED when I finally started making enough money to drop off my laundry instead of doing it myself (dropping it off cost $30/month, btw), and the super cheap massage place I frequented every few months that still gives off major hand job vibes. To get to my old apartment, I took the train I passed out on multiple times on my morning commute due to stress and exhaustion caused by my job in book publishing I left two years ago (that job also caused me and other coworkers to miss our periods!).
My first job out of college (in my industry) paid $27,500 a year. If that sounds like not enough money to live on in the city, you’re right. It isn’t. I spent 4 years living at home, commuting 4 hours every day to Manhattan and saving money. By the time I moved to Queens in 2014, I had paid off 60% of my $100k student loan debt and written 4 books for HarperCollins (under a pseudonym because it's a genre I don't even read) solely for the money. By then, I was making $38,500 a year, which is still not very much considering NYC is the second most expensive city in the world. I very much remember the years of having to walk 22 blocks every morning to save the (at the time) $2.25 subway fare, considering a weekly $5 cup of soup for lunch a “treat,” and stealing rolls of toilet paper from bathroom stalls at work because it meant one less expense.
I also remember the shitty people I dated and the shitty sex. Oh how I remember the shitty sex.
I’ve dated Russian bankers who claimed that me using toys “threatened their masculinity,” insufferable photographers who had more opinions on obscure music than an actual sense of self, freelance film dudes (For the love of god, save yourself. Never date these men; they are man-children) who were about as exciting in bed as a Wes Anderson movie.
I fucked office temps, sommeliers, a literal sex addict who worked in international aid, advertising executives, a guy who worked at an Apple store, a producer at a very well-known television show that’s still on the air, a special ed kindergarten teacher (I mean, come on, just bend me over already), Broadway dancers, and a very memorable voice-over actor in Williamsburg who ate my pussy for 4 hours straight on my 28th birthday. Him and the kindergarten teacher were great in bed. Everyone else? [farting noise]
And during the three years I spent in Astoria, while I fucked a lot of lackluster men, I was busy building a career. I was editing 900 pages a week at a thankless job that gave me zero weekends off and kept telling me I was not good enough (despite the books I worked on selling really, really well) so they had an excuse not to promote me (the company was hemorrhaging money). I was taking the N/W train every day, which is a job in and of itself. I have no idea how I did it, but I carved out small slivers of time to write for magazines on the side. My then boss made it very clear that she was not supportive of this, but I didn’t want to stop. Between being broke, dating stupid people, and suffering at a job that was working me to death, sex writing was the only thing that made me happy.
I used to see a therapist near Central Park South once a week on my lunch break, my only reprieve from my hellish job. During our first session, she asked if I could not eat the salad I had brought because it was distracting.
I looked at her, dead-eyed, and said, “I have to fucking eat.”
“Well,” she replied, “At least I know you’re assertive.”
No joke, that therapist went on to get murdered by someone, which was a shame because she was a really good therapist. Ah, New York City.
With a dead therapist and an unsupportive, micromanaging boss who apparently didn’t want me to have a life outside of work (which is very often the case in book publishing, unfortunately), I decided I had to leave. I was scared shitless to make a drastic career change, but I wanted to write and I wanted to get my fucking period again. I found a generic front desk job at a tech startup that paid more than what I was earning as an editor making a name for herself in the industry (outside of my boss, people actually liked me and my work a lot) where I'd write more. At the time, I had purple/green/blue/pink hair and took my mom out to lunch in the East Village to break the news to her. I was ashamed that I was leaving the industry I had specifically gone to NYU for. As someone with an incredibly blue collar, middle-class upbringing (both my parents didn't go to college), I grew up to value stability. I was taking a huge risk by trying out this whole freelancing thing.
"I don't want you to be embarrassed that your daughter left a career as an editor to become a receptionist," I told her at some outdoor cafe near Tompkins Square Park. "What will you tell our family when they ask about me?"
"I'll tell them what I've always told them when they ask about you: that you're a writer," she said.
I saved a photo from that day.
At my new job, I dyed my hair black (I had dyed it blonde for the interviewing process, but, as much as I loved it, bleach made my hair fall out and I didn't want to look like Cynthia from "Rugrats") and wore jeans and combat boots out of necessity. Between buzzing people in, stocking the kitchen, and literally shop vacuuming overflowing toilets, I sat at my desk and wrote. A month later, my first story got picked up by Cosmo. Six months later, I became a contracted contributor to Playboy.
At this time, I started dating the person who I thought I was going to marry and he lived very far away. Every Friday night, I commuted 3 hours upstate (one-way) to spend the weekend with him. On Monday mornings, we’d wake up a little after 5 so I could be in Union Square by 9. I did this for a year. Actually, what I should say is: I have no idea how I did this for a year. The constant back and forth was incredibly draining.
About 6 months into my new job at the tech company, I got approached by the then VP of marketing. Because I sat at the front desk, I knew all of my coworkers by name and was friendly with almost everyone. One day, this VP came over to ask a question about our company’s commuting benefits or something and he happened to ask where I worked before I came onboard, thinking I had been a front desk person somewhere else. When I informed him that I had ten years of experience as an editor, he asked why the hell I wasn’t working on his team. Soon, I started editing marketing materials. By the time things were getting serious with my partner upstate and I had plans to move, through a series of circumstances, I was given a full-time remote position in marketing. Between the new remote gig and discussions of engagement rings, I got rid of my apartment with the intention of moving upstate.
And then the breakup happened. With nowhere to live, the idea for this trip was born. Since I left Astoria last June, I’ve lived in Boston, Asheville, Austin, and Denver, I’ve driven across the country on my own, I went on the best (and most impulsive) vacation ever to Hawaii, I got published by 4 new publications (including my dream one, New York Magazine), I got published in print for the third time, I’ve been interviewed by Buzzfeed and (soon) national television, I’ve fucked some truly gorgeous (inside and out) people, and I've figured out a lot of things for myself. I’ve been hustling, y’all. And I’ll continue to hustle.
I went from making minimum wage and editing other people’s work to having financial stability for the first time in my life and traveling across the entire country while writing things I'm passionate about. I recognize I had a ton of privilege while moving up this ladder, but a lot of blood, sweat, and tears went into it, too.
Between my jam-packed schedule while I’m back in NYC and looking back at all the work I’ve done over the last ten years, I decided I need a tiny break.
Next weekend, I move to Chicago for the last “big” leg of the trip (6 weeks!). After Chicago, I fly to LA to pick up my car and drive up the PCH to Portland, where I’ll stay for 3 weeks before driving back to the East Coast. The gift I’ve decided to give to myself right now is self-care. In Chicago, I plan on being on my phone less, reading actual books more, learning how to box, cooking more (and I don’t mean just heating up veggie burgers and eating potato chips, DANA), going to the beach, and writing some chapters of a new book. I also plan to masturbate more.
Because here is the big announcement (one of a few more to come over the next couple weeks): I’m going to start doing sex toy reviews on my website.
This decision happened after learning that toys—just like so many other products featured in magazines—are given false praise by online publications in exchange for a cut of sales. As someone who believes in only providing 100% truthful information about sex, masturbation, and sexual health, I consider this practice to be Grade A horseshit. So I’m going to start writing some myself.
Not even a day after coming to this conclusion via a conversation with a PR person I know and love (who is just as horrified by this practice as I am), I was asked if I wanted to become a brand ambassador for a company called MedAmour, a startup whose focus is making the act of buying sex toys less scary, ensuring quality control, and helping those with medical conditions that can make sex uncomfortable or downright impossible (including vaginismus, endometriosis, etc). Its stock is carefully curated so that new customers aren’t overwhelmed or intimidated, and products are appropriate for those just beginning to broaden their sexual horizons. You will not find any scary-looking, intimidating, or "advanced" toys on this site. The owner had the idea for this company when she realized sex therapists were recommending certain toys to their patients, but weren’t recommending specific brands or where to go. And that led to three big problems: confused people not knowing what exactly to buy, finding cheap toys on Amazon (Where the quality isn’t controlled! Never buy sex toys from Amazon—many of them aren’t body-safe!), and/or going to large brick-and-mortar stores and being so overwhelmed that toys never got purchased.
I’ve been asked to partner with some companies in the past and they were either things I was not particularly interested in (if I get offered a partnership with a tampon company one more goddamn time), didn’t seem beneficial to people who follow me, or the company owners had a less than stellar reputation. I truly believe in MedAmour’s mission and I want to support a woman-owned-and-operated business. If I can write honest toy reviews and then be able to offer discounts to people who want to buy the toys I recommend, then that is a win for everyone. I'm not doing this for the money (and the money is very small, trust me), I will only recommend toys I absolutely love, and I was going to write the reviews anyway, with or without this partnership. I want to destigmatize toys (after all, they are a HUGE part of creating an amazing sex life--check out tip #3!), provide people with accurate information about them, and support a business whose mission I fully believe in.
And to prove that I’m not being a shitty “influencer” dipshit who’s peddling crap that sucks, my first giveaway with MedAmour is going to be… A WOMANIZER STARLET (worth $89!). If you’ve followed me for a while, you know that I have talked about this toy for years and consider it a must in any vulva-haver's collection because, get this, it’s a CLIT SUCKER. Here’s me raving about it in September of last year, where I say, “It’s almost indistinguishable from real oral sex, you can orgasm in under 3 minutes, and you don’t have to listen to a cis male talk about The Smiths afterwards.”
It’s also the toy that consistently makes me squirt when combined with penetrative sex. On this trip, I’ve squirted while using it with two different former-Bible-thumpers-turned-agnostic-nonmonogamous-people! It is truly the Lord’s toy.
I look forward to bringing you my signature blend of candid, informative, and, at times, humorous real talk about a bunch of sex-related products. I can’t wait to talk about my love of dilator sets (I used one as a teenager!), anal play, and the newest clitoral and penetrative toys on the market. It's gonna be so much fun and I hope you feel empowered to try something new!
I made it to Arizona, the first place where I’ve had to make sure I brought all of my luggage inside so that my dildos wouldn’t melt in my car. The heat here is an EXPERIENCE.
The rest of my time in Denver was great. My sex friend and I exchanged gifts before I left. He made me 4 mixed CDs (my car has a CD player, lol), including one he titled “DanaMash,” which starts with the song “Sex Machine” and includes at least 6 songs about big booties. In return, I made him this:
You're damn right I framed it.
You’re just going to have to trust me on this one, y’all, but please know that I only give praise when it is deserved (more on that below!). I shall miss that dick (and the dude it is attached to).
But yes, I drove to Arizona so that I could stop at the Grand Canyon. I did the classic thing where I thought about my life and how small I am in the universe. Many people have existential crises at the Grand Canyon and, to be honest, it’s kind of hard not to. I thought about my place in the world and what I want from my life. And that made me think about the conversations I’ve been having lately about autonomy, bravery, and creating a joyful life—and a big part of that is creating a joyful sex life.
I recently had a friend tell me she wanted to delete Tinder because, over the last 6 months, had only met “one cool guy and two cool girls.” I laughed really hard at that. Then I told her I had been on multiple apps since last October and had met three cool men in Boston, one in Asheville, and one in Denver. I think there’s a perception that dating just comes really easily to me and the hot men I fuck cross paths with me solely because of luck. There’s also a perception that at the beginning of this trip (eight months ago), I just flipped a switch and gained a really amazing, exciting sex life. Or that I've always had one because I am a sex writer.
Holy shit NO. No, no, no.
It’s so not that. Creating this life took a lot of hard work, a lot of failure, a lot of gaining life experience and learning from mistakes, and a lot of sticking to my guns even when it was really, really hard. Up until four-ish years ago, I was having pretty crappy sex—the kind of sex people would describe as “average” and come to know as all that sex could be.
I no longer have crappy sex. And I want other people to no longer have crappy sex. Thinking of people accepting the kind of sex I tolerated for so long actually makes my heart hurt.
When it comes to how and why I have a great sex life, I really thought about it. And then I pulled together these ten reasons why my sex life is the way it is:
1. I don’t follow the sexual script. When I went to the conference for sex therapists and educators last month, the idea of a sexual script was explained to me by Dr. Laurie Mintz. It’s something we all kind of know, but I’d never heard it articulated before. The sexual script goes like this (for couples where one person has a penis and the other has a vulva): kissing, light touching of breasts or vulva, oral, penetration, orgasm by person who has penis. The end.
This script, I’ll admit, is something I followed for years. Then I thought… why does sex have to look like that every time? Why am I following a “formula” that doesn’t value me as an equal partner (i.e. I’m not guaranteed an orgasm in order for the sexual encounter to be considered complete)? Then I did the best thing I ever did for myself: I abandoned it.
The way I think of sex now is: let’s write down on a whiteboard all the things that are sexual or sensual. Sure, it would include all the things I’ve mentioned in the sexual script, but it would include some other things, too: things like manual stimulation (fingering), anal, massage, cuddling, spanking, playing with toys, mutual masturbation—and so much more. What if you and your partner looked at this board and decided together what you wanted to do? “That looks fun,” “And so does this!” etc. etc. Sex could be performing oral on each other and that’s it. Sex could be a massage and then some anal. Sex could be a spanking session and then getting fingered. Sex could be every single thing on that list! At the end of the day: what would sex look like if there were no rules? Throwing away the script has vastly improved my sex life.
Also, there is a hierarchy in terms of what makes you come and that’s bullshit, too! Apparently, orgasms from P-in-V sex are “better” than those achieved in other ways. But I come the hardest from being fingered! Does that make me “broken”? No! Are orgasms from some things more intense and feel better than others? Yeah! Is it different for everybody? YES. Let’s stop thinking that any method of achieving orgasm outside of penis-in-vagina sex is inferior. [One of my funniest memories: I once had an ex who said he “felt bad” that the last sex we ever had before we broke up was anal. (So if you put your dick in the hole that’s an inch and a half north, it would have been “more meaningful?” LOL he was such an idiot.) I was actually SO happy he said that to me because it made me feel so much better about the fact that he is my ex.]
2. I am incredibly comfortable naked. Now listen. This one took a while. I was once an eating disordered person, so I very much remember what it was like to hate my body and not be comfortable in my skin. And then something happened when I was 24 (when I was already five years recovered from bulimia!) that changed me. I was dating some guy who lived in the Lower East Side and after a sex session, he got up to get something from the kitchen and I walked across his apartment past him to the bathroom to take a shower. (Ah, the days of Young Dana, where she used to sleep over—I was so sweet back then. Now I’m that cartoon sound effect that’s like zoooooom and then there’s a cloud of dust.) It was such a simple thing, but in the moment, I was terrified. Then thought to myself: why am I scared? Why on earth would the person who just had sex with me be turned off by me walking around his apartment naked? He… just had sex with me. He’d already seen me naked. So why did I care now?
And that’s the thing: if someone has had sex with you, they’re already into what you’re workin’ with, so why be self-conscious? (And if they’re not—if they make any sort of negative remarks about your body, make sure to wish them good luck with their rib removal surgery that will enable them to suck their own dick while you're on your way out the door.) Plus, something I always think of is how I’ve noticed “flaws” (I put this in quotes because I don’t believe in any physical attributes being flaws—but I do recognize there are things considered as such by society) on my partners: birth marks, hair growing in weird places, low-hanging balls (this guy I’m thinking of in particular was also the best pussyeater I’ve ever encountered), whatever. I notice these things about my partner as like a “oh hi there, physical attribute,” but I don’t judge them. And I realized that's how people must think about the things I have felt weird about with my body in the past—sexual partners may notice my weird pinky toes or the fact that my body hair grows like fuckin’ Tim Allen’s beard in "The Santa Clause" or my back tattoo (hey, it was 2007), but they don’t care about them. And half the time, I’m sure they don't even notice that shit in the first place.
Getting comfortable with your body takes a lot of hard work and practice! It’s not an overnight thing! Try sleeping naked for a night or two (this was super helpful to me—and I felt so uncomfortable at first). Walk around your bedroom naked while you do chores. Get stoned and dance around naked (my personal favorite). Also, another way I got comfortable naked around another person was introducing an element of relaxation to it! I’m a big fan of massaging people. If you’re going to grind on a person’s naked body, don’t you want to explore it a little bit first? Don’t you want to learn what feels good to your person? When I engage in a sexual relationship with someone, I always take time to massage them. This may make people feel a little vulnerable and I get that. But I promise you that if your partner can’t make you feel comfortable while giving or receiving a massage, sleeping with them probably isn’t the best idea.
3. I consistently use toys during sex. Repeat after me: sex with toys is not inferior to sex without toys. Say it again. And one more time. Thank you. Because something we need to remove from our society is this notion that for sex between a penis-haver and vulva-haver, a penis and a vaginal canal are the equivalent pleasure centers. They’re not. We should be teaching in sex ed that it’s the penis and the clitoris. And guess what? During penis-in-vagina sex, it’s important to have clitoral stimulation, whether that comes from someone’s hand or a toy.
Some toys I recommend during sex are: the Vesper Crave (it’s a necklace and surprisingly powerful—but quiet—vibrator) because it’s long and thin and is small enough to be used in any position without getting in the way, the Womanizer Starlet during any position where the pubic mound of each partner isn’t pressed against the other (ex: doggy, missionary where the man is maybe on his knees instead of flat on top of his partner, man standing/woman lying down on edge of bed, etc), and a bullet vibe with a remote during any position that involves lying on your stomach (like anal). Before understanding the importance of clitoral stimulation in penetrative sex, it baffled me as to why women would ever enjoy receiving anal or analingus. What was the point? And I was right—there is very little point when it comes to anal play on its own if you are trying to achieve orgasm. BUT WHAT NO ONE TOLD ME IS THAT ANAL PLAY WITH CLITORAL STIMULATION IS INCREDIBLE. A bullet vibe on your clit during anal? Holy cannoli. Amazing. And a toy on your clit while getting your ass eaten? It’s practically heaven. My point is: don’t shame toys. If you subscribe to the idea that only sex without toys is worth having, I can guarantee you that you’ll be having fewer orgasms. Anything that can get vulva-havers to come more during sex is a win in my book.
4. I embrace the things that make me feel sexy. There is nothing more fun to me than buying lingerie. It is my ultimate self-care. And I know this can be scary—like buying a bathing suit. But think of it this way: trying on lingerie is dress up. And it’s not to be seen by just anyone, unlike if you were going to the beach. If you think of it that way, it takes a lot of the pressure off. I buy very fancy silk lingerie from places like Journelle and I buy super inexpensive stuff for, like, $12 from random sex toy stores or online at Yandy.com. It doesn’t matter. I also identify as a sub and truly enjoy doing things that will psych up my Dom. I had someone recently ask if I could wear a cotton thong in a light color so he could see how wet I was. Running out to buy one before I saw him? A huge turn-on and very thrilling. Seems like it was something for him, but it was absolutely for myself. Sending pictures and videos also makes me feel sexy! Never send one solely for the pleasure of someone else (unless you truly get off on it). I’m not one of those people. Exchanging pictures is only fun for me if it’s mutual (AND ONLY WHEN I SOLICIT THEM).
5. I have masturbated. A lot. I would say I masturbate as much as a teenage boy, but that’s bullshit. I masturbate as much as a teenage girl because they’re just as horny; we just don’t talk about it. But yes, I masturbate because the best sex comes from teaching your partner how to get you off. When it comes to achieving orgasm, no style is a one-size-fits-all kinda deal. We all like different things. One of my least favorite things is when a guy tries to finger me the way his last partner liked it. (I have literally grabbed the wrist of a guy fingering me WAY too fast and hard, looked him square in the eye and said, “I’m not going to come like that.”) My clitoris is a snowflake, dude! Let me show you what’s gonna work. And that’s the thing—if I don’t know what I like, how am I supposed to articulate what I need to my partner? Masturbation leads you to be more in tune with your body and better equipped to teach your person how to get the job done. Knowledge is power!
6. I play. I don’t box myself in. I identify as a sub, but BDSM sex is not the only kind of sex I have. Not by a long shot! I like everything—slow and tantric, rough and hard, silly, adventurous, the list goes on and on. I see so many people who find themselves saying, “I like x, so we only do x” and that really limits you. I’m not advocating for abandoning the things you know you like (I’ll never abandon BDSM!), but how will you know what you do and don’t like if you don’t play? My saying is, “Always try everything twice… or else how will you REALLY know if you like anal?”
7. I don’t fake orgasms. Ever. Faking orgasms is a gross disservice to both yourself (because you deserve to come) and your partner (because you’re not teaching them what you need in order to come—and how are they going to learn otherwise?). When you fake an orgasm, it tells signals to the other person that the technique they used makes you come… and then they will continue to do it… and then you will continue to what? Oh right. Not come.
Most vulva-havers feel pressure to fake it when they feel their orgasm is “taking too long.” Here’s what I’m going to say to that: it will take as long as it needs to take. There is no reason to feel guilty. I guarantee you that your partner would rather you have a genuine orgasm if it means servicing you for another ten minutes than you faking it. I promise. And if you’ve ever blown a penis-haver, YOU KNOW that sometimes they take a while, too! We should all be entitled to whatever amount of time we need in order to come. And sometimes that time will be shorter or longer than others. Sex isn’t a science! Porn has taught us that people should come multiple times in, like, ten minutes, but we all know porn isn't realistic. The vast majority of the time the women are faking (even the lesbian porn!) and the men are taking breaks and gettin’ fluffed between takes, y’all.
8. I bring up testing. Absolutely no sexual experience is worth the price of me contracting an STI. Even the absolute best sex of my life. I’ve been asked many times by others how to bring up testing with partners—especially casual ones. “I can’t exactly talk about it with the guy I bring home from a bar,” they tell me. And my retort is always, “But… can’t you though?”
My go-to line is, “Hey, I have a six-month rule. If you haven’t been tested within the last six months, I don’t play with you. No exceptions.” The perception may be that it’s too off-putting, but, in reality, I get a lot of respect for sticking to my guns and for prioritizing my health and my partners’ health. I’ve only had one person be scared off by it (and if someone is scared off by that… do you really want to sleep with them anyway?). Mostly, I get people who promise to get on their shit and then a few weeks later we play! I can’t enjoy sex when my mind is worrying about STI risk. If I know I'm being safe, I can be fully present and happy. I’ve also had friends ask me, “Well how do you know if they’re telling the truth if they say they’ve been tested?” And to that I can only say that I use my best judgment. I can tell when people are lying. (And, honestly, only a sociopath would lie about something like that.) Most of the time, people offer to show the receipts, which is great! And if they don’t offer and I feel the need to ask for them… that means I don’t really trust them and shouldn’t fuck them.
9. I only date people who value my pleasure. Years ago, I had plenty of sexual experiences where I didn’t come and said it was “fine.” (How many times, vulva-havers, has that happened to you? It’s a very common experience.) After all, I had grown up on the cultural messaging that women weren’t meant to come every time, that orgasm is harder to achieve for women than it is for men (wrong), and that sex ended when the penis-haver orgasmed. (Vulva-havers can be brought to orgasm as easily as penis-havers. There are actually studies that support this. If you're a vulva-haver, think about how "difficult" it is for you to orgasm via masturbation. The idea that you can't orgasm as quickly as a penis-haver is a crock of shit, right?) Then, after about four sexual experiences with a guy I never came with, he finally went down on me, got me THIS close to orgasm… and then he gave up. I almost kicked him in the head. Never again, I said to myself. I would never date someone who didn’t care if he got me to orgasm. Over the last 8 months, with the exception of one person, I have only dated givers, which are men who get off on their partner getting off. (And that one person who wasn't a giver got kicked out of my apartment.) My most recent partner (who received the best dick award!) refused to come until after I came at least 3-4 times. After knowing that there are men out there who are like this, I will never settle for anything less. And pleasers are a lot less hard to find than you think they are.
10. I don’t settle or tolerate bad sex. You deserve someone you’re super attracted to. You deserve someone you don’t feel just “meh” about. (Sex also feels better when you’re super turned on! You’re wetter, which makes things more comfortable, and, believe it or not, when you’re more aroused your vaginal canal can expand up to 7 inches to accommodate a big ol’ dick!) You deserve someone who cares about your pleasure. Guess what I do when someone clearly doesn’t care about getting me off? I fucking leave. This attitude took a while to develop, too, because it takes some major balls to get up, put your clothes on, and tell your partner to quite literally fuck themselves. (And please know that I recognize the risk of kicking someone out or leaving if you or the person are in a house or apartment alone—pissing off a man can come with consequences, but I am very fortunate that I haven’t run into any problems. That also comes from dating people who I know would stop if I asked them to stop.)
Now how did I learn all this? Well, as my friend Sophie said, I have a high threshold for failure. It took a lot of bad dates, bad sexual experiences, and bad partners to teach me what I like and what I deserve. I have waded through the bullshit, and, trust me, still continue to do so! It just gets easier to find the good people the more practice you have. So don’t fret if the joyful, amazing sex life doesn’t come immediately. Just like your orgasm, it takes time.
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.