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.