When people tell me they hate dating, they’re tired of the slog, don’t feel like they’d be attractive to a potential partner, or are still hurting from a breakup, I don’t tell them “Be more positive!” or “Oh, you’re being silly. You’re great!” or “It’s time to move on!” Instead, I tell them, “Take a break.”
You know why? Apps are always going to be there. Pussy’s always going to be there. Dick’s always going to be there. There is no rush.
But everyone feels the pressure to be partnered, and it makes sense, right? If you’re partnered, you’re seen as “successful,” like you’ve unlocked some sort of achievement. If you’re single, there must be something wrong or you’re not trying hard enough. If you’re partnered, you’re better than your single friends. If you’re single, your goal should be to ultimately become partnered. It’s just like how we view bodies: if you’re attractive by society’s standards, you’re “good.” If you’re not, you “should” be working on achieving it. And the harder you work, the better you are. The more you’re worth.
“Work harder, be better” is what we’re told constantly.
I recently had to tell a fellow overachieving lady a hard truth: successful women often get frustrated by dating because in any other situation, we know that if we put a ton of effort into something, it will yield results. If you work hard in school or your career, you get a payoff. Dating doesn’t work like that. You can put in a ton of effort and nothing is guaranteed to you.
[Side tangent: One of the reasons we’ve been taught to worry about our attractiveness is because it’s associated with attracting the male gaze. One of the reasons we’ve been taught to worry about being partnered is because it’s associated with holding the male gaze. Annually, the beauty industry is worth $445 billion, the weight loss industry = $66 billion, and the wedding industry = $72 billion. Internalized misogyny and capitalism are a real bitch, y’all.]
The truth is there's no shame in being single and there's no shame in being celibate. I actually respect you a helluva lot more for focusing on yourself until you feel better (and feel better about dating) before you return to it than I do for continuing to date and have sex and being miserable. Plus, when you’re not feeling great, both the date and the sex is going to be bad anyway.
It’s okay to take a break from dating.
I will say, though, that I have a hard time following my own advice because I have the sex drive of a 15yo girl. (I know the conventional saying is “a 15yo boy,” but guess what? Teenage girls are just as horny as boys. It’s just that no one talks about it.)
The problem with having no stability as you travel from place to place is that… you have no stability. If you’ve been reading my blog for a while, you’ll see that I’ve experienced a lot of ups and downs. And when there’s no stability and you’re working 4 jobs, it can be very taxing on the mind.
Shortly after I arrived in Chicago, I started working straight through from 7am to 11pm. I didn’t get more than 4 ½ hours of sleep per night for a solid week and a half. I was falling into perfectionist tendencies and black-and-white thinking. I must date and talk to people on apps. I must be on social media for my job. I must follow through on all projects I promised myself I’d do outside of my day job (freelance, blogging for other companies, writing my book). I don’t have time to eat actual meals. My basic sex and food needs? Booty calls and takeout will have to suffice.
And then I crashed. Hard.
Last week, I crashed so badly, I only left my townhouse to shuffle down the street to the drugstore, buy some diet iced tea, and drink it in bed while looking at my phone for hours. I couldn’t relax. I was exhausted but wired. Eventually, I put my phone down and laid on my side, one arm over my pillow and the other under it so I could hug something while I half-slept, my cheek pressed to the cool fabric. My body was going into Bad Brain mode, something I only experience during extreme periods of stress. This is what was going through my head:
That's when the Universe was like "oh fuck OFF, Dana" and threw me a bone.
Before going to bed, I picked up my phone to set my alarm and saw a text from one of my closest friends in New York, Dave.
When I lived in NYC, I was at Dave’s apartment pretty much every other week. Dave’s heard every dating story I’ve ever had; many a tale has been told while we’ve eaten pepperoni and mushroom pizza with his dogs on our laps. I have the key to Dave’s apartment, which I offered to return to him before my year-long journey.
“Keep it,” he told me. “That way you know you always have a home here.”
Dave’s text was a request for my address in Chicago because, completely unprompted, he wanted to send me a gift. I smiled, the knot in my stomach loosening slightly, and went to bed. I slept eight hours for the first time in ten days.
When I woke up, I snapped out of it. My usual way of thinking came back to me: any “desire” to be thinner and partnered because I will be “better” because of it—complete bullshit. I’ve been miserable as a thinner person and miserable while in a relationship. My worth isn’t determined by my body being considered attractive to a man or the fact that a man has chosen me as his partner.
That afternoon, I FaceTimed Cecilia, my therapist extraordinaire. I told her about my friend Sophie’s suggestion—one that was given to me after I confessed I had noticed my hair falling out in clumps—to not do any work besides my 7am – 4pm day job for a full week. No freelance work, no research for my book, no work for the two companies I decided to partner with.
Cecilia agreed that it was an excellent first step. “What else can you do this week that you know will make you feel better?”
I blurted out the answer immediately. "Not date."
The truth was clear: I had become the exact type of person I encourage to take a break from dating. I hated it, though, because, like I said earlier, I am hornier than a rabbit... in a chatroom in 1995 with their mom’s credit card. I told her I really wanted to date, but knew it wasn’t a good idea right now.
Get yourself a therapist who, when you say, “If I don’t have sex in over a month, I start to go insane,” replies, “I get that.”
But taking a week off wasn’t going to kill me.
Cecilia's homework for me was to make a list of things I’d do this week to prioritize sleep, nutrition, and physical activity—three things I know improve my mental health.
I started to set two alarms: one at 9:30pm telling me to get ready for bed and one at 10pm telling me to go to bed. I ordered food with actual vegetables in it. I went to Pilates and aerial classes 4 days a week. I got out of the fucking house.
I hung out with my two friends in Chicago (an amazing couple I knew for a while on the internet who turned into real-life friends). They’re both incredibly kind, hilarious, and generous, and introduce me to the coolest, hippest restaurants in Chicago. Many of the most exclusive restaurants here are hidden and you have to be in the know to even be aware they exist. There have been plenty of times where I’ve shown up to where I *think* the restaurant is, only to text one of the pair, “I think I’m here? WHY IS EVERYTHING IN THIS CITY A SECRET”
The three of us went to High Five Ramen, a 12-seat ramen establishment not even open yet that somehow has an hours-long wait (we were at the front of the line, however, cuz my pal has connections). That same night, we got drunk and ordered McDonald’s (something I’ve never done in my life, believe it or not) from the corporate headquarters on Randolph Street, where you order from a touchscreen and can sample items from various international menus. I read an incredible book on my rooftop overlooking the Chicago skyline (video below), I got a pedicure, I put together a care package for my friend in New Zealand, I bought a card for my dad, I wrote this blog post (the only writing I do for me and not for money).
I also had a soul-nourishing hangout with my friend VP, who has visited me a few times while I've been on this trip. I always love seeing him. We’re both writers and we’re both comedians, so what the fuck do you think happened when we walked by a wig store with a “going out of business” sign in the window?
I also went to Bad Hunter on my own and did my favorite thing: sit at the bar, order a full 3-course meal, and sip a fancy mocktail while writing on my laptop. The next time you see someone eating alone and feel bad, I promise you they are enjoying every second of no one fucking talking to them while savoring their meal.
I took a day off from my day job, woke up when it felt good, got a latte at Sawada coffee (seriously, the best espresso I’ve ever had), shopped at the brand new Glossier pop-up shop around the corner, visited Warm Belly Bakery, and then went to… my favorite place on earth. I’m not exaggerating. Because there’s one in my home city.
My favorite place in New York City—even ahead of Veselka (Ukranian diner), Levain (the best fucking cookies you’ve ever had), and Van Leeuwen (I dream about their honeycomb ice cream)—is a place called Aire Ancient Baths. In the middle of nowhere, right next to Chinatown, is an underground spa the size of half a city block filled with hot pools, cold plunges, a salt float pool, and an aromatherapy steam room. Only six exist in the world: New York, Barcelona, Sevilla, Almeria, Vallromanes… and Chicago. How Aire Chicago existed before Aire London, Aire Copenhagen, or Aire Paris (all slated to open within the next two years) is beyond fuckin’ me, and I was floored when I found out there's one within walking distance of my Airbnb. If someone on Tinder hadn't told me, I never would have known.
Being at Aire Ancient Baths is one of the most relaxing experiences of your life. It’s even more relaxing after taking two edibles before you walk in.
When the 24yo I mentioned in my last post texted me asking if we could meet up on the Friday night of the week I promised to devote to myself, I suggested another day when all I truly wanted to do was bang him again.
You don’t have to wait until you’re perfect in order to date (because then you’ll never date!), but you do have to wait until you feel better.
I wanted to write this post to show that the self-love, sex-positive chick sometimes has bad body days. She also has to constantly create boundaries with herself and others. She gets dating fatigue, too. She gets tired as hell, too. She sometimes gets sad about cultural ideas surrounding relationships and dating and even falls victim to them sometimes. And that’s okay. She, like everyone else, just needs to hit the reset button sometimes.
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:
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 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.
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:
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 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.
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.