Dating in Chicago

I haven’t lived in Chicago for all that long, but the one thing I can say with complete certainty is that it is the easiest city to arrange a threesome. But we’ll get into that later.

The funny thing about Chicago is it wasn’t even on my original list of cities I wanted to try living in when I started planning the trip around this time last year (wow, that’s weird to think about). Bear in mind that at that time, I had never lived in a new city before in my entire life. I had picked cities at random that sounded interesting to me. I do recommend doing this, but I do not recommend doing this and not running it by friends who actually know the places you pick.

For example, Savannah (Georgia) was originally on my list until a very kind friend informed me that I would probably be murdered there.

“But it’s next to the beach!” I argued. “I love the beach!”
“Have you ever seen the movie Deliverance?” he retorted.

I crossed it off my list.

And then I kept hearing from people who have known me for a long, long time that they could picture me loving Chicago. I had to go during the summer, they insisted. I made it work.

When I landed in Chicago, I felt sick to my stomach. (I found out later that I had contracted E. coli.) I was vomiting, shitting my brains out, had a splitting headache, and a high fever. My third night in Chicago, I called my friend HB (Hawaiian Bryan from my last post) from the bathtub at midnight because my chills were so bad and enjoyed yet another story of him being the dumbest human alive (he fell out of a tent and rolled down a hill).

The best thing my therapist has ever said to me happened last year right after I had found myself single with nowhere to live and had come down with mono and Lyme’s: “The only thing that can get Dana Hamilton to slow down is her getting incredibly sick.”

Miserable in bed, I realized I may have too many irons in the fire. Over the last month, I’ve agreed to partner with both a sex toy seller and a Canadian condom company that I love (and y’all never heard of, but I will soon change that), met with my agent and figured out the premise of my next book (he wants me to write a proposal while in Chicago so he can shop it around this winter), committed to writing sex toy reviews on my site, continue to post on this blog weekly and continue to freelance. Oh, and I also have an 8-5 day day job in marketing. Beyond the E. coli, I was run down.

I took a little break from social media, a lot of hot baths with half a bag of eucalyptus Epsom salt dumped into ‘em, and 2 days off from my day job as pure evil flowed through every orifice of my body. I reminded myself that if I don’t do some serious self-care and take a break from some things, the book that I’m super passionate about will never get written. But I decided to stay on dating apps because, believe it or not, dating is my self-care. Let me explain.

One of my friends in LA spoke with one of our mutual single friends who had asked her how I maintain a positive attitude while dating. “I think Dana just loves people,” she told her.

It’s true. I fucking love people. Sure, sometimes people are pretty awful, but people can be fascinating, ridiculous, sweet, and humorous, too.

Being a writer with a remote day job is tough because both require you to spend long stretches of time alone. And I am a very extroverted people person. My day job and my dating life allow me to interact with the world around me. Writers need that. That’s why dating is self-care for me.

But dating in the Midwest is one of the most interesting experiences I’ve had on this trip so far. At first, it was very challenging, but then I got the hang of it.

I once told a hookup that the only time I’m not horny is when I’m very, very ill. But I guess that was a lie because even when I had pneumonia (you know, that illness where your lungs start to fill with fluid?) in high school and was weak and feeble as Old Rose™ in Titanic, I jacked off pretty every single one of those 30 days I was out of school. With this bout of E. coli, in the small stretches of time between each prayer for death I whispered into the sky as I laid dead-eyed on my bed, I was arranging dates and booty calls on apps for when I was feeling better. I hadn’t had sex in a month and was starting to unravel. 

And that’s where I encountered my first road block.

Because I booty call women and date men, I separate my apps: Tinder is for women and OKCupid is for men. If I blend the two in any way, I get fetishized by men and looked at as "not as serious" by women.

I sometimes struggle with the label “bi” and prefer the term heteroflexible. Because I only fuck women when I’m horny and don’t want to deal with men’s bullshit. That’s the god’s honest truth. 

These are real profiles I've encountered from men in Chicago:

I can't.

Homeboy WASN'T EVEN BRITISH

Legit the most terrible human I've ever encountered

LOLOLOL

I have no words

Now don't get me wrong--I can very happily have sex with only men for the rest of my life. I love men. I crush on men. I fall in love with men. When I date a man and really like them, I think about ‘em. Women? Never. But do you see now why I sometimes like to fuck women?

I also just like eating pussy, you guys.

Because I was only looking for hookups (no strings, I never see you again, take care), I created an honest profile that said just that and was shocked by the amount of bites I had gotten. Because if I had that bio in NYC or Boston, the line to my apartment would be out the door.

But women don’t operate like that here.

For a solid few weeks, I was getting very few matches, which has never, ever, ever been my experience on Tinder. I was confused, but not disheartened. There is an ebb and flow when it comes to dating. By that time, I was feeling better anyway and wanted to make up for the week I lost sick in bed. I wandered around the River Walk, went shopping in Wicker Park, sampled incredible food at Gilt Bar, Clever Rabbit, Big Star, Windy City Café, Jerk, Piccolo Sogno, and Bombobar. I savored an incredible glazed donut from Stan’s and drank the best iced latte of my life at Sawada Coffee. I went to a shout-along of the movie Clueless (where the audience quotes all the dialogue together) at The Davis Theater with some friends. I enjoyed the roof deck of my incredible 3-story townhouse and read books in the sunshine. I found a great workout. I went to Up and Up at the Robey Hotel and took in gorgeous views of the city.

This is my self-care

I bought this very fancy dress at Moon Voyage in Wicker Park and have nowhere to wear it to, so if you're a hot dude or chick in Chicago or Portland and wanna take me out, slide into my DMs or something.

This is a reminder that when dating seems a little slow, it is the perfect time to go out and fucking enjoy yourself.

But I was still dying for a fun, hot hookup. My clit was pretty much tapping on a microphone, going, “Is this thing on?”

My Tinder bio was essentially the equivalent of “FREE PUSSY," so why did I have so few matches? I went out with an amazing long-time internet friend turned IRL Chicago friend and told her about THE CROSS I HAD TO BEAR. She looked at me, laughed, and said, “Welcome to the Midwest. Everyone here wants to get married.”

“But where are my fun lesbians at?” I whined.
“They’re looking for a wife,” she replied.

I realized I hadn’t “dated” women for all that long and was still learning the ropes. (I’m putting dating in quotes because dating right now is me asking someone if they want to come to my apartment, order takeout, smoke a bowl, and fuck around.) 

Then I remembered one of my lesbian couple friends in NYC. They have promise rings that are made of silicone so they don’t have to take them off while they lift weights. If that’s not the most lesbian thing ever, I don’t know what is.

Okay, so finding a lesbian to bang in the Midwest was going to be tricky. Fine. I started to wonder if I could fuck a couple.

But here’s the thing about couples looking for a third in the Midwest. It’s a lot of people who live in the 'burbs and are thinking of it solely as a way to spice up their boring Midwestern marriages (because they don’t know of any other ways to do it). None of them have any experience, and I am no one’s first time and I am no one’s experiment. Ever. ​

So many women aren't upfront about being part of a couple looking for a third, so they spring it on you after presenting a profile that's just them on their own. And that's when I'm like LOL no bye

There are also a LOT of these kinda profiles

I’m not having my pussy eaten by someone who’s never done it before, Susan. I’m not your present to your boyfriend, Brenda. I’m not schlepping out to the suburbs, Janet. I love myself more than that.
​
I said to one woman recently hey, if you want to have one-on-one time with me beforehand so you know what’s up, I’m down. Then we can invite your boyfriend to the party. She was SO enthusiastic--excited even--because she had always wanted to do that. But her boyfriend wasn’t cool with it. First, he threw a hissy over the fact that he couldn’t watch (that ruins the experience, BRAD, because then your girlfriend feels the need to be performative and isn’t going to be present and actually enjoy herself, trust me). Then, he admitted that he didn’t want her to play on her own under any circumstances. I understand that, but I also don’t at the same time. I would hope any partner of mine would know that sleeping with a woman (in this context) doesn’t mean anything, be supportive of my sexuality and desire to play alone, and not hold me back from an experience I really wanted.

I was cockblocked by an insecure dude. And that’s fine—because I don’t want to sleep with an insecure dude under any circumstances. Bullet dodged.

When there are experienced couples, it’s great, but it’s very hard for me to find myself attracted to both parties. There’s a lot of this going on:

And OF COURSE on the fourth day of Mercury in retrograde, I accidentally swiped left on two hot dudes looking for a third (I love MFM) on OKCupid. Goddammit.

Women weren’t working out and couples weren’t working out. And then it hit me: you know who isn’t typically looking for a relationship? Dudes much younger than myself. Cut to me going on a date with a twenty-four-year-old.

[The last time my friends gave me the amount of shit I got for doing this was when I fucked a dude named one of the worst names on the planet. Think "Gilbert," but a thousand times worse.]

But there were five great things about this 24yo:

1. He’s former military. I have a known weakness for these men.
2. He’s incredibly intelligent and well-read. Like, “I don’t have internet in my home by choice because I like to read”-level well-read.
3. He’s very charismatic and fun to talk to and he knows it. I dig confidence.
4. His brother once described his body type as “Ukranian powerlifter.”
5. The moment I saw him, I was like yep. Yep, yep, yep. I wanna turn that face into a bike seat.

It’s incredible how clear my mind becomes once I’ve had sex. It’s like a tranquilizer dart.

Anyway, the next day, I went on a date with someone I talked to so much via text, I was like fuck it, let’s just have a phone call instead. And then we were on the phone for an hour. A fellow comedy writer, we met for tacos and laughed and swapped stories for a few hours. Then I introduced him to Insomnia Cookies (based in NY! I didn’t know there was one here!) as I groaned while consuming that Stan’s donut. At the end of the date, we both agreed that we didn’t feel a sexual connection, but enjoyed each other’s company a lot (at least I did) and decided to hang out again as friends.

I love texting with other comedy people!

I started getting more dates once I understood that the men and women here are looking for more of a serious thing. It didn’t make me mask who I am as a person (I’d never change myself for the “benefit” of someone else), but it did influence the way I communicated and how much I shared about myself. Then things started to get easier. Plus, the married, nonmonogamous, experienced women started coming out of the woodwork (it just took ‘em a while!), and that was extremely helpful as well.

So far, I love Chicago. The dating scene has been great, the food is incredible, and, honestly, as a New Yorker, it just feels like home. I’m excited what the next month will bring.