I’ve landed in Portland, a place where there is an abundance of Tibetan prayer flags (but no Tibetan people to be found), a surplus of people wearing deodorant that does not contain aluminum, and way too many culturally appropriated white dreads.
That said, I don’t mind it! Portland was just as easy to figure out as Chicago. In short, Chicago is Brooklyn. Portland is what would happen if Denver and Asheville had a baby. As much as I loathed Asheville (and the dating here is just as bad, if not worse), I liked Denver so it all evens out. I kinda feel about Portland the way I feel about Austin—the dating scene is severely lacking (toxic, even), but besides that, it’s not a bad place to live.
I’ve also already accepted that I’m not going on dates with any Portland men because they’re all insufferable Sad Boys™ and I love myself. Things have been picking up a lot in terms of freelance—I have 3 essays due this week—so I decided to use these next few weeks in Portland to write. [This decision was made easier by the fact that I just had a bunch of fabulous sex in Chicago and then get to see my Denver sex friend next month. I’ll survive.]
But with the trip wrapping up soon (so soon!), I realized I had all these stories from the road that never made it into an “Eat, Drive, F*ck” post because they didn’t fit in anywhere. But they’re all stories I love to tell, so here they are. Some of my most ridiculous moments from the road.
I arrived in Austin a few days before my 30th birthday. And I celebrated the way any woman should celebrate: hooking up with a very recently retired NFL player.
I told this guy I had his picture, knew his full name, and had security cameras at my condo complex, so I felt okay with him just coming to my place (please be safe when hosting first dates or booty calls; make sure you get all this info, tell the person you have all this info, and ALWAYS TRUST YOUR GUT). I had a good feeling about this guy and he was totally cool with everything. And it turned out great! He comes over and he is very handsome—6’5” and, because he’s retired with nothing to do, all he does is go to the gym. This guy could easily blow my back out, he’s very pretty in the face, and, my favorite, he’s hilarious.
The thing I liked about him was the first thing he admitted to me is that he is very dumb. We smoke a bowl, Postmated some tacos (Taco Joint in Austin is really good), and out of nowhere, he sighs and says, “I would be really bad at Wheel of Fortune.” He came out with a bunch of other winners like when I asked what he wanted to drink and he replied, “Water. I’m a real waterhead.” I don’t even know what that means, you guys.
Because he was 6’5” and built like Big Foot, he kept knocking over shit in my apartment. I was dying laughing the entire night.
“I don’t think you’re dumb at all, honestly. Because you’re funny,” I told him. “You have to be smart in order to be funny.”
“No, you don’t understand,” he said. “Dana, I went to one of the worst colleges in America.”
After dinner, I was cleaning up and he cornered me in my kitchen, pretending he was trying to get around me to throw something out. “Don’t do that,” I told him. “It’s very intimidating to have a 6’5” man standing this close to me, towering over me in my kitchen. If you want to kiss me, you have to ask.” I wasn’t annoyed because I knew what he was trying to do and I definitely wanted to kiss him, too, but I had to lay down the rules nonetheless.
He sincerely apologized before saying, “Now that I think of it, if I had a 7’5” guy coming toward me, trying to kiss me, I’d be intimidated, too.”
I am a sucker for people who can make me laugh. I walked him over to my bed.
We were making out and he had his hands down my pants when I realized, oh shit, I never asked him about testing. So I pulled away and asked if he’d been tested within the last 6 months.
“Oh…” he said, his face dropping. “We… don’t really do that here.” (Welcome to Austin, y’all. This was so common with the dudes I had met there and why I only slept with women from there on out.)
To his credit, instead of pressuring me to hook up, he asked if he should leave.
“Oh!” I exclaimed. “Just because I don’t feel comfortable having penetrative or oral, it doesn’t mean we can’t do other things!” I reminded him I’m a sex writer and we could get creative! He was down.
Cut to me naked and draped across this behemoth’s lap while he spanked and fingered me. If I remember correctly, I’m pretty sure I came three times. Then I got some lube and jacked him off while we made out. He. Came. So. Much.
See? It’s easy to have fulfilling sexual interactions that are outside the “norm” of what sex looks like (I hate saying that because there is no fuckin’ norm). Getting spanked and fingered for hours even felt more intimate than him just getting on top of me and having some missionary action. All parties were left satisfied. It was a fabulous early 30th birthday present.
A few weeks later, I was cleaning and realized there was some of his cum on the gravity blanket I have on top of my bed. I own a weighted sleep blanket because, you know, I’m an Italian greyhound during a thunderstorm.
Being the idiot I am, I tweeted about this.
Five days later, I got this email:
I have never cackled so loudly upon reading an email. Because wtf did Gravity blanket think happened? Do they employ a serial masturbator and this isn’t the first time he’s jacked off on a blanket? What is going on at that factory where it’s a jizz free-for-all?
I sent back the following email because I believe the truth will set you free.
That's right. I'm a fucking athlete.
I posted the interaction on my social media and the fucking bosses over at Gravity Blanket’s biggest competitor slid into my DMs.
I couldn’t believe this was happening. But, just like my sex toy collection worth close to $3,000 would tell you, I never say no to free stuff. And I knew my brother was thinking about getting a weighted blanket because we’re all terrible sleepers in my family.
And that’s how my brother got a free blanket.
As a former dancer whose rheumatologist once referred to her joints as "incredibly loose and flexible," I'm essentially a walking marionette puppet. I have a problem with hyperextension all the time. It’s bad because since I have double-jointed hips and shoulders, I never feel it when I’m doing it. At one yoga class in Asheville, I clearly fucked up and ultimately developed two golf ball-sized lumps on my lower back.
I was in so much pain I felt it even when I smoked some of my strongest weed. I couldn’t sleep.
The thing about Asheville is it’s so small that there aren’t many massage places and the ones that do exist are often fully booked up as a result of the scarcity. But even then, a massage would help to alleviate some of the pain, but what I really needed was bodywork—massage that incorporates trigger points to stop your muscles from spasming.
After hanging up with my fifth massage place who told me they couldn’t fit me in in the near future, I stayed in bed because the shooting pain in my legs made it hard to walk and started mindlessly swiping on Tinder. And that’s where I found someone who said they’re a licensed massage therapist in his bio. I almost cried when we matched.
HEY, I messaged him. I FUCKED UP MY BACK AND REALLY NEED YOUR HELP.
He asked if I was being serious. He asked, for clarity, if this was purely a transactional, platonic thing. I answered yes to both. He almost lost me when he asked if I wanted to come to his studio that he runs out of his house, but when I said I didn’t feel comfortable doing that, he said no worries, he could come to me and bring his table for an extra $10. I would have paid a thousand at that point.
I lived with my Airbnb host at the time and she works from home, so I felt totally safe inviting him over. He had also volunteered his license number so I could look him up and confirm that he’s never had any complaints filed against him (which was true—he hadn’t). When he showed up, he looked incredibly professional in slacks and a button-down shirt. I told my host what was going on—because LOL a strange man shows up with a massage table—and it was totally fine.
He gave me a massage in my bedroom with the door open. “Wow, this is really bad,” he told me after pressing on the lumps on either side of my spine. “You’re so lucky you found me because I’m the only masseuse in Asheville who does bodywork.” I silently thanked the Universe when, after an hour, he almost completely fixed my fucking back. The next day, it was 90% better. I was floored.
I texted him and asked if I could have one more session before I took my flight home; I feared sitting for hours in a cramped airplane seat would flare up the spasms in my back. He told me if I came to his home studio, he has a hot tub that he asks clients to sit in for a half hour before the massage because it results in more effective pain relief.
I told him since I was staying in Asheville during the winter for 5 weeks, I hadn’t packed a bathing suit. He said he wouldn’t want me to wear one anyway because the chemicals used to wash bathing suits are bad for the hot tub. Plus, I’d be in the room alone, so I didn’t need to feel weird about it. He said if I wanted to listen to any music while I was waiting out my 30 minutes, he’d set up Spotify on his sound system so I wouldn’t be bored. I sent him one of my favorite albums.
A few days later, I took a Lyft to his place and it was obviously legit. He had a room set up in his house with his table, there were plastic sandals and a robe for me to change into. Downstairs, in a renovated garage, was the hot tub. He set up the music, set a timer for a half hour, and left, closing the door behind him.
After about ten minutes, I started laughing. I was swimming around naked in the hot tub of a stranger I met off of Tinder, in a fucking basement, belting Etta James’ greatest hits. There have been a few times on this trip where I’ve been like, how did I end up here, and this was one of those times.
When I got back from Hawaii, I was fucking bummed. What made it worse was one day I woke up with another ruptured ovarian cyst. This is something that had derailed my time during my first leg of the trip in Boston, where I ended up being hospitalized.
I had bought expensive tickets to the symphony and really needed the distraction from my post-vacation blues. And I didn’t want this cyst to fuck up my trip the way it did in Boston, so I did a kinda stupid thing. And by kinda, I mean very.
When I land in a new city that doesn’t have legal weed, the first thing I do is put on all my dating app profiles “420-friendly cough I’m new here cough help a sister out cough wow I must be coming down with something.” Soon after I arrived in Austin, I met up with a rugby player at a coffee shop. He had asked me what I wanted and my answer was “Gorilla Glue and an indica so strong it will knock me on my ass.”
This idiot handed me both in identical, unlabeled plastic bags. So when I smoked up right after I had called my Lyft to the symphony, I thought I had smoked the Gorilla Glue, a light, giggly hybrid.
Narrator voice: That was not what I had smoked.
At first, I was like oh shit, but then I gave myself a pep talk. I was like, “All right, Hamilton. This will be fine. All you have to do is get into the Lyft, it will take you right to the symphony, and you will walk right in. That’s all you’re responsible for. Easy peasy.”
But when I was dropped off, the venue was nowhere to be found. It turned out the address on my ticket was the address of the box office, which was in a really bad part of Austin. There were lots of people walking around, talking to themselves. It was also 8 at night, dark out, and I could barely keep my eyes open. I was high as shit. The last time I was this high on an indica, I was at the Seattle airport, where putting cream cheese on a bagel felt like open heart surgery.
I kept looking on my ticket for the correct address, but the only one listed was for that damn box office. I was pissed that I had to admit defeat and take a Lyft home. But when I looked at the app, I saw a car wouldn’t be able to get to me for 5 minutes. The area I was in was so bad I didn’t feel comfortable waiting for that long there.
That’s when I saw a police car doing surveillance across the street.
I knew they’d know I’d be high—they’re fucking cops for chrissakes—but I decided to take the chance. If there’s anything Dana Hamilton is not, it’s a QUITTER. I was determined to get my ass to that symphony.
I jauntily jogged over and waved at the police officers (god, I was high). The one in the passenger’s seat rolled down her window. I knew I could play up the fact that I wasn’t from there and got lost on my way to the symphony. I had a New York license and my ticket to prove both of those facts.
I was too high to conjure up tears, but I made my voice crack as I explained the situation. “I don’t know where to go!” I said mournfully.
“Do you know what they’re playing?” the female cop asked. Thank god I remembered they were playing Beethoven’s Fifth as part of their program. Once she did a quick Google search, she found it. She turned to the cop in the driver’s seat. “It’s at the Long Center,” she told him.
He looked at me. “Ma’am. You have two options.”
I braced myself.
“You can either call a cab to come here and we’ll tell them the address or, if you don’t mind riding in the back of a police car…”
He didn’t have to finish before my dumb ass hopped into the back.
Fun fact about police cars: the back doesn’t have any cushions. It’s just hard metal.
The other cop asked to hold my purse because she had to check for weapons in it and thank GOD I had just taken all the weed and paraphernalia out of my bag the day before. I had been walking around with two baggies of weed in there for about a week because I just plumb forgot after buying from that rugby player.
On the drive over, the female cop kept asking me questions, which I hated answering because I was the kind of high where I wasn’t sure of the volume of my own voice.
“Where are you originally from?” she asked.
“NEW YORK I DROVE HERE ACTUALLY HEH HEH I LIKE AUSTIN SO FAR CAN’T BELIEVE I GOT LOST”
There was no fucking way they didn’t know I was high.
When we got to the symphony—which, mind you, was a 15-minute drive away, so I never would have found it—there was a long line of cars, so the cops asked if I didn’t mind hopping out right there and walking up the small hill to the symphony. I thanked them profusely (which was still probably me shouting) and walked inside.
When I got to my seat, I texted my friends “Just rode in the back of a cop car. Will explain later” before putting my plane on airplane mode since the performance was about to start. After it was over, it was fun when I turned my phone back on and essentially received many texts demanding what the fuck I just said. Now sober-ish, I realized something. There were definitely people in that line of cars that saw a woman exit the back of a cop car and walk directly into the symphony.
If you have ever believed that white privilege doesn’t exist, please remember that I once approached law enforcement high off my ass and was given a courtesy ride.
The only “bad” date I had in Chicago was with a guy who lived TWO BLOCKS FROM ME in Astoria when we both lived there. I’m putting “bad” in quotes because I had a great time
Now outside of my trip to Hawaii, I drink maybe 5-6x/year and when I do, my absolute limit is 2. Because I drink so infrequently, I usually tell people on dating apps I don’t drink because EVERYONE wants to meet for a drink. So this New York guy asks me out to dinner at some fancy French bistro. I say sure.
We’d talked on the phone a few times and it was fun chatting with him. He made a reservation for 8:30 and asked if we could meet at 7 to take a walk around the city. He said he’d pick a landmark near the bistro for us to meet at. I knew something was off when he texted around 6:30 saying he was already at a bar across the street from the restaurant. But whatever, I thought to myself, a landmark is a landmark. I ask if I should come over now and he says yes.
I show up fifteen minutes later and this man is VISIBLY hungover. I’m talking flushed to the point of being red-faced and he is sweating profusely. He’s also just finished a drink and when I walk up, I catch him ordering another.
This guy didn’t know why I didn’t drink; he never asked. For all he knew, I could have been sober. I was so floored by him thinking this was acceptable behavior (regardless of whether I was sober or not), that I was like okay, this is not going to go anywhere because what he did was so fucking rude... I might as well mess with the guy and entertain myself.
I pop a small edible and tell him we’re going to Portillo’s. Portillo’s is essentially the exact opposite of a fancy French bistro. It’s like what would happen if a hot dog stand fucked the 3-story TGIFridays in Time Square and I love it.
It’s a twenty-minute walk and by the time we get there, I am comfortably and mildly stoned. This motherfucker wants to get a drink. At Portillo’s. After I stare at him incredulously, I tell him if he wants to have a drink, it has to be a strawberry daquiri or else I’m leaving. He fights me on it, but in the end, he’s sucking down the contents of a boozy, frozen hummingbird feeder. I’m enjoying a chocolate cake shake (a vanilla milkshake with a slice of chocolate cake BLENDED INTO IT—amazing) happy as a pig in shit.
When I’m on a bad date and know it’s going nowhere, I ask deeply personal questions to make myself laugh. “How many times a week do you jack off?” is a known favorite. This guy is so drunk, he admits to me that he’s cheated on everyone he’s ever dated and still hooks up with his ex who is engaged to another person. I am eating all of this up (including a hot dog and French fries).
At the end of the “date,” which only lasted an hour, he asks if I want to come hang out with his friends at a bar and I tell him I’m going to walk home. “Ah shit,” he says. “I fucked up, didn’t I? I’m never going to see you again, am I?”
I double over laughing on the street. I’m still a little stoned and there are literal tears in my eyes. “You show up violently hungover and tell me you’re a cheater. What the fuck do you think?” I walk home and continue to laugh to myself. I can’t even call the date bad because at the end of the day, the guy never said anything rude to me, I had some company while I ate dinner, and I didn’t invest much of my time. I took it for what it was and it still makes me laugh when I think about it.
Like I always say: I don’t have bad dates, just good stories.
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.