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.
The day I left Chicago, I went to the apartment of the man I wrote about in my last post. I spent my remaining three hours getting devoured like he was on death row and requested my pussy and ass as his last meal. I tend to lose track of time when I hook up with this person, so we set an alarm to ensure I’d get a car to the airport on time, but when it went off, I said, “Two more minutes.”
That’s how I feel about Chicago as a whole. I just wanted two more minutes. I really, really didn’t want to leave.
My friend and I were a little nervous about me getting to the airport because my Lyft driver took a solid ten minutes circling the block trying to find us. Once she picked me up, she then proceeded to tell me look out the window because “isn’t that baby so pretty!”, didn’t know if New York City was on the east or west coast, and asked why Chicago sex friend wasn’t coming with me. I texted him this and told him next time, if given the option, I’d pack his mouth in my carry-on because I know what it do. [insert tongue emoji a thousand times]
I adored Chicago. I… liked it better than Boston, which is saying something. I’m still moving to Boston at the end of the trip, but if it wasn’t so far from my friends and family, I’d sign a lease in Chicago in a heartbeat.
I lived my best life there. I stayed in a gorgeous (and very expensive, but worth it!) 3-story townhouse with a roof I ate lunch on every day. I got Classpass and found my love for Pilates again. I ate at many of the best restaurants in the city, wrote at the best cafes, walked around and shopped in the best neighborhoods, hit up the beaches, and went on dates with some fabulous people. I can’t recommend spending 6 weeks in Chicago during the summer enough.
Let’s break it down, once again, into my blog’s namesake, shall we?
I ate a lot here. Chicago is an incredible eating city; nothing will ever top Austin, but I could almost argue Chicago’s on the same level. I didn’t have a single mediocre or disappointing meal here. I also didn’t cook here… at all. I went out for every dang meal.
Gilt Bar: The cacio e pepe… oh my GOD. Get it and the chocolate cream pie.
Honey Butter Chicken: Fuckin’ fantastic. After 5 weeks in Asheville, I vowed to never eat pimento cheese EVER AGAIN, but their pimento mac and cheese was divine.
Bad Hunter: If you go here and don’t get the potato fry bread (with burrata and cherries), I’m pretty sure you’ll get arrested. The menu is seasonal (though I think the fry bread is a staple), but if they still have it, get the beef kabob on polenta, too. Great mocktails, too.
Little Goat Diner: Get the crudité platter (it comes with homemade naan with everything seasoning on it) and the “One Twisted Sundae.” The latter is a fudge brownie topped with pretzel-flavored ice cream, caramel sauce, whipped cream, and pretzel pieces. It was divine. I came back and got the turkey club, which was so damn good and, remember, I’ve tried the best delis in NY and Boston.
Clever Rabbit: My friend told me their burger was “stupid good” and she was right. Best burger I’ve eaten in my life.
El Metro Cantina: These tacos are better than the ones I had in Austin. Get the chicken tinga and the pork. Their red and green salsas are legit.
High Five Ramen: Get there early (like 4-4:30pm). The wait can get up to 4 hours and it’s a twelve-seat establishment. Get the classic ramen, half-spice. It was delectable.
The Violet Hour: Really cool speakeasy in Wicker Park. I love how it’s designed. Strong drinks.
Café Baba Reeba: I usually don’t go for tapas places, but everything on this menu was delicious. I loved the fried chicken thighs, beef kabob, stuffed mushrooms, and burrata. I enjoyed this place so much and couldn’t make it there during a week I was on deadline, so I had it delivered. I ordered the chicken and mushrooms again, as well as their garlic potato salad and Brussel sprout and manchego salad. Incredible.
Gyu Kaku: There are a few of these across the country and when I’m back in NY, I will *absolutely* be hitting it up. I love Japanese barbecue, but sometimes it can get expensive. This place was very reasonably priced and all the food was delicious. Get the jelly sake. It’s so weird and yummy.
Stan’s Donuts: Classic glazed is where it’s at. Game over.
Sawada Coffee: Their black camo latte made me see God. It’s matcha and espresso, which, yes, I KNOW it sounds disgusting, but it turns out it’s DELICIOUS and tastes like chocolate. Get it with almond milk instead of regular milk. Just trust me.
3 Arts Café: Chicago sex friend recommended this place and holy shit. It is my dream place to write. I thanked him profusely. (Get their fries with garlic aoli and their warm chocolate chip cookie + a cup of coffee. Yes, I am aware that I eat like a raccoon.)
Beaches: I tried going to Oak Street beach, but it was closed for an event, so I walked 15-min north to Long Avenue Beach. I was warned by a friend that it would be crazy busy and, yep, it was. But I enjoyed it nonetheless. I liked Kathy Osterman Beach much more. It’s a little bit of a hike and is nicknamed “the gay beach,” so, out of respect, I shamelessly flirted with a very attractive woman while wading up to my waist in the FREEZING COLD water (and got her number).
Movie theaters: I took the blue line to Logan Theater and enjoyed this super cute place until the film “Eighth Grade” DESTROYED ME. I also went to a “Clueless” shout-along (where the audience all quotes the dialogue together) at The Davis Theater with my friends and it was fabulous. The theater was gorgeous.
Workouts: I highly recommend Ascend for their classic reformer class with an instructor named Sheridan; she’s a sweetie. I also like Pilates Pro Works’ machine classes if you want a challenge. If you like aerial silks, Air is fabulous. Challenging, but incredibly fun.
Wicker Park shopping: Wicker Park is a very cute area. It’s essentially the NYC East Village equivalent. I went to Penelope’s—a super affordable option—and bought a cute lil’ cotton off-the-shoulder black romper that makes me feel like Audrey Hepburn if she was into toddler cosplay. I also went to Una Mae’s (slightly more expensive) and bought a delicious white cotton shirt and long, dark navy bodycon dress. But my favorite shop was Moon Voyage (very pricey, unfortunately), where I impulse bought an expensive slinky black dress for absolutely zero reason (I’ve been dying to find a dress like this for years though) and this light pink silk tie-front top.
I wore that shirt to coffee with Chicago sex friend and he told me it was very distracting. I told him it was payback for him sales technique-ing me. :)
When I first got to Chicago, as I’ve mentioned in previous posts, I went on a date with a 24yo for the first time in my life. I’m a 30yo woman who, all throughout her twenties—with the exception of someone who was 26 when I met him—dated older, this was an experience that made me laugh at myself. But, as I’ve written earlier, he was great. Incredibly intelligent and eloquent and a total cutie. But our schedules just didn’t sync and we fell out of touch. No harm, no foul. He was cool.
Next, I went out with someone hilarious, but there was no sexual or romantic spark for either of us. I did want to hang out again as friends, but, alas, I couldn’t find the time. He was cool, too.
Then I went on a date with a super adorable woman in an open marriage who I really liked! She did pole-dancing and I really wanted to go to a class with her, but then she had a family emergency… and then my job got crazy… then I got strep throat… and our schedules didn’t mesh. I felt horrible because I truly did want to hang out again—I wasn’t trying to pull a slow fade or anything—and I actually did want to redeem the “one free threesome” coupon she kindly offered to me on behalf of her and her hot ass husband, but, AGAIN, it just didn’t work.
About three weeks before I left Chicago, I met the gorgeous dude from my last post who I ended up hanging out with for the rest of my time here.
I do not regret this choice.
In all, everyone was fabulous! The Chicago dating scene is great! I only went on one “bad” date, which I’ve written about in the next post. And it wasn’t even bad because I thought it was hilarious.
Chicago, you are tied for first place with Boston. Not sure how that happened, but you are. I rerouted my drive home to return for a few weeks next month. Maybe I’ll be living there permanently in a few years… Who knows.
Two Fridays ago, I texted my group chat with two really good friends like I always do. We all live in different states and text every day. That morning, I told them I had a really good date. “I’m exhausted because we didn’t get to bed until 3:30,” I told them.
“I’m sorry, did you just say we?” one of them asked in a voice note. “As in… you let someone sleep over?”
“WE ALSO CUDDLED,” I admitted. “I DON’T KNOW WHO I AM ANYMORE.”
The truth is he was incredibly kind (and didn’t snore), I felt horrible making this sweet man take a car home past 3am, and he said he wanted to eat my ass in the morning. I mean… how could I say no when breakfast is the most important meal of the day?
Taking my own damn advice from my last post served me well. My week off from dating was the perfect reset button. Once I spent a week devoted solely to taking care of myself, I was able to hop back into it with a positive attitude. I found the fun again. Because if dating isn’t fun for you, you probably shouldn’t be doing it. Circling back when you feel better is important because the experiences you have will be ten times better than if you force yourself to date while feeling shitty.
Cut to the Thursday night after my week-long break. I had a good feeling about this guy before we met because he laughed at my silly jokes and spoke very intelligently about misogyny—and not in the showboat-y kinda way men who very loudly declare they’re feminists do. I'd told him about how I recently had to set some idiot’s ass straight after he claimed friendzoning is a thing. (I actually wrote something for Cosmo a few years ago about why it’s not.) I sent him screenshots of the conversation and afterwards he texted, “That was exhausting. I don’t know how you kept talking to that guy.”
After he said that, I put my phone down, went into the bathroom and proceeded to bonsai my bush into a cute upside-down triangle before the date. Yanno. Because I respected him so much.
I also knew he worked in Sales, an industry requires a certain personality type. You have to be ambitious, an excellent conversationalist and a fairly extroverted people person to do well in that particular career path. I’m someone who values social adeptness and emotional intelligence above all else when determining who I want to spend my time with. Plus, this dude was a Leo. A Leo who works in Sales meant this date wasn’t going to be boring at all.
We met at an amazing tapas place called Baba Reeba (so, so delicious) and I experienced two unexpected firsts:
Y’all also know how hot HB, the only decent man I met in Asheville, is:
And I’ll just say my Denver sex friend has an overall appearance just as impressive as his dick, which earned him this coveted award from me:
I wasn't intimidated by any of those men.
But when I met up with this date at the foyer of Baba Reeba, it was the first time I ever felt like someone was waaaay out of my league. I already knew he was going to be hot because of his pictures on Tinder, but when I saw him in the flesh, I was like oh fuck. This is not going to bode well for me. That’s the God’s honest truth.
He looked better than his pictures, and I’m not sure what kind of witchcraft made that possible. This kid looked like a brunette, bearded Zack Morris who powerlifts and models when he’s not at Bayside chopping lumber in the back of the school. I was thrown off my game. I didn’t feel self-conscious per se, just realistic—something along the lines of if this guy doesn’t want to go home with me, I wouldn’t be surprised. Not a reflection of me or my self-worth, but just like… I get it.
2. He is as direct as I am when it comes to communication.
I’ll admit #1 was stupid for me to think because this man knew exactly what I looked like. It’s not like I arrived and appeared vastly different from my pictures or videos. I was still intimidated though. When I’m intimidated, I’m not my usual, painfully direct self who says stuff like “So this was fun. Do you want to fuck around now?” when the bill comes.
My assumption that this date would end with an attempted half hug (that’d I’d pull into a REAL hug because I’m not a QUITTER) and vague promises to hang out again was strengthened when my date suggested a unique Chicago thing to do, I said “I’d love to!” and his response was “maybe you could go with a friend.” My pussy essentially sat down in a director’s chair and shouted THAT’S A WRAP into an old timey microphone.
Sex was clearly off the table, but I was like hey, I’m still going to enjoy this date. We ate some mind-meltingly good food and talked. He was clearly very intelligent, a good storyteller, and very kind. And then, before I knew it, the place was packing up. That’s odd, I thought to myself. We had only met at 7, but some places in Chicago close on the earlier side, so I brushed it off. My date then excused himself to use the restroom and looked at my phone. It was 10:30.
The best part of the date wasn’t the fact I was having such a nice time that three and a half hours flew by. The best part occurred about mid-date, when this man looked over at me and said, “I assume you want to see me again,” which is the boldest, ballsiest, most Leo thing I've ever witnessed. I scream-laughed. “I can’t believe you just said that!”
Now here’s the thing. If someone said that to me and they were wrong, I would give them more crap than a Port-A-Potty at a chili festival. But he was 100% right. I did want to see him again. And he could tell I did.
That is some shit I would pull. I’ve been on dates where people have told me I’m “refreshing” to talk to and they're having a lot of fun and my response has been “Well, of course you are because I’m great.” Now I felt like I was on a date with myself.
The tables had fuckin’ turned. This man had major BDE (Big Dana Energy), so I didn’t pull any of my usual tricks. Right before we left the restaurant, I asked what he wanted to do so that if he preferred to end the night, he had an out. When he told me there was a place close by with a cool rooftop, I was like okay, he wants to continue this, but I still couldn’t tell if that was the extent of it. After all, this guy was so damn polite, he told a story at dinner about how he was once catfished, stayed, and asked the person if they wanted to have a drink.
THAT IS HOW KIND THIS FUCKER IS.
So I still didn’t directly ask if he wanted to fuck, opting instead to tell him my townhouse has a private roof deck with a great view of the city. When he agreed to come back to mine and put his hand on my bare knee during the Lyft ride over, I was like okay, Dana. You no longer need to be in disbelief that this hot man is interested in fucking you. It’s a possibility, Hamilton.
In the car, I told him I was surprised he still wanted to hang after he suggested me going off and doing something with a friend earlier on in the night. He then told me he was doing something he does at work called “keeping behind the pendulum,” a tactic used to show clients you’re not too eager too early on in an interaction.
He fucking sales techniqued me.
“Listen,” I told him. “I know you don’t believe in this stuff, but… that was the most Leo move of all time.”
We got to my place and I showed him the roof deck, but I was only wearing a silk dress and it was chilly out, so we went inside after a few minutes. It was only when we were both sitting on my bed that I asked if he wanted to fuck me. He said he did. I admitted that under any other circumstances, I very directly tell people I want to fuck them. I didn’t with him because I truly couldn’t tell.
He then reminded me that I had asked him to come home with me and the moment we came inside from the roof deck, I put my hair up.
Touché, friend. Touché.
After we established mutual emphatic consent, we still kept talking because we liked chatting with each other! But eventually I told him we had to stop because I really wanted his clothes off. There’s that direct Dana Hamilton communication we all know and love. We stopped talking.
Sometimes, inexplicably, there are people who are so in tune with their partner’s body--even during sex on the first date!--they will start doing what the other person wants just as they open their mouth to say it.
“S—” was all I’d manage to get out before he’d spank me. The last time I experienced this kind of sexual ESP was a hookup in Williamsburg three years ago whose birthday present to me was a floral bouquet with lots of peonies in it and four hours of oral sex.
Speaking of spanking, this dude was a pro and I told him that. Most people hit way too hard (like they don’t understand I’m an actual human person and not a meat sack) or way too soft (like their hand is dead at the wrist). Some hit too high, near the lower back, which neither feels good or makes a satisfying sound. But I had to give this guy zero direction. “It’s an art and a science,” he explained later and I cackled.
There was also a moment during the hookup where I was kinda floored by how good at sex this guy was and then remembered how competitive he is. Former football player, current powerlifter, works in Sales... I was like huh. I like competitive men. Because, to them, getting me to come is like scoring points in a game and I want my sex life to be a damn pep rally.
[I know that analogy doesn’t make sense because you don’t score points at a pep rally, but I DON’T KNOW SPORTS STUFF, ALL RIGHT?]
Four orgasms and one 69 session later (usually one of my least favorite positions because trying to focus on blowing a guy while they’re doing an excellent job of eating your pussy is like trying to take the SATs with a pencil covered in bees), my Chicago date and I kept trying to go to bed, but couldn’t stop making out. Hooking up with a good kisser is a goddamn treat; if someone’s good at kissing, I don’t want to stop kissing them. Bad kissers frustrate me because they turn me into a bad kisser, which I know I’m not. Kissing is a dance. If the person you’re dancing with is a bad leader, you start tripping over your feet. I can’t tell you how many men have attempted to waltz with me and made me look like that recent video of Lindsey Lohan where she appears to be doing a solo audition for the Greek Rockettes and no one is watching.
We finally went to bed at 3:30am and I woke up a few hours later for my day job. Having your ass eaten in the morning is a risky move because sometimes morning tummies are gurgle-y. I had also had a few glasses of sangria at the tapas place and never drink. Keep it together, Hamilton, I told my asshole during my quick shower. My GI tract, after being alerted by my brain how hot this dude was, cooperated. “Don’t ruin this for her,” my stomach told my butt. After returning to bed, this handsome gentleman gifted me another two orgasms by eating my ass like it was two honey-baked hams and he had just given up on keeping kosher. I then clocked into work and pounded some cold brew with him before he called a car right before my daily morning video meeting with my department.
Five minutes after he left, I received a text message containing the sentence "I clearly want to see you again.”
^^ What a great ending line to this piece that would be. But this is not where this story ends.
A few days later, I mentioned I had written this post. Though I had written about him completely anonymously (no name, image, or identifying personal info), it still somehow felt wrong posting it. After all, besides my post about my trip to Hawaii with Homeless Bryan (HB), whose blessing I received before and after I wrote it, there hasn’t been an entire “Eat, Drive, F*ck” post devoted entirely to someone I’ve met on the trip. It just felt weird.
“Wait, wait, wait. You wrote a blog post about me?” he texted. “Can I read it?”
I was hesitant. Because this guy would essentially be reading the equivalent of a Yelp review of his dick. Though I knew everything I had to say about him was incredibly positive, I tried to put myself in his shoes. Would I be freaked out if I read something like this a professional writer had written about me after a first date? I didn’t know. And the last thing I wanted was for this guy to run screaming for the hills when I was leaving Chicago in just a few short weeks and really wanted to see him again.
I’ve always said that if a man gets freaked out by me being exactly who I am, I shouldn’t be sleeping with them anyway.
But… I’m also a weak woman when it comes to beautiful men who eat me out like it's the Last Supper.
[Holds up bread] "This is my body." [Holds up wine] "This is my blood." [points to my pussy] "And this is my muffin."
Plus, I get it. It takes someone who is very secure in who they are (and respects what I do) to be excited about appearing in my writing. Lord knows not every man I've met has been like that. In fact, very few have been.
“Will you judge me for it?” I asked.
“Okay. Gimme your email address.”
[gives it to me] “Or you could just bring it with you when I see you Wednesday night.”
“Omg no” is what I typed back, but what was actually happening was me flailing on my bed going oh god oh god oh god that sounds horrible what the fuck am I gonna do with both my palms pressed to my forehead.
“I would be mortified,” I told him.
I couldn’t stand this charmer.
“I will quite literally sit on the ground, bent over, my face in my hands,” I told him. “You know. Like a real professional.”
“Could you be naked though?” he texted back.
He had found my Achilles heel.
“Ok you drive a hard bargain," I told him. "But I'm in.”
On Wednesday, after we met up at a speakeasy called The Violet Hour in Wicker Park (really cool place), he came back to mine, we fooled around, and afterwards, as promised, I let him read this post off my laptop while lying naked on my bed. Sitting there watching him read would make me curl up and die so I kept my hands busy by kneading the back of his thighs and calves with warm oil from a massage candle.
He laughed at all the appropriate places and complimented my use of memes. When he read my line about competitive people thinking bestowing orgasms is like putting points up on a scoreboard, he exclaimed, "That's exactly what it's like!" My anxiety subsided, and I was happy. The latter may have been due to the fact that my hands had traveled further up his legs and were now on his fantastic ass, but who’s to tell, really? Who's to tell?
“This is great!” he said before we made out for hours.
I let him stay over again. That Big Leo Energy will get ya every time.
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 regular contributor to Playboy and her work has appeared in VICE, Cosmopolitan, Marie Claire, New York Magazine, Teen Vogue, and SELF, among other publications.