All the people I've fucked in 20 years

Can sex be casual in your 30s?

Seasons greetings from my traveling house of vomit and snot. As many of you have been following my journeys through an ever-rotating deluge of daycare plagues, I won’t bore you with the messy details of the last few weeks. All you need to know is the first one hit me while solo-parenting for the first time - a relentless stomach virus that had me and my son on a simultaneous colon cleanse, resulting in many onesies being thrown away and many rounds of itsy-bitsy spider shout-sung from the toilet.

Then he brought home a two week death rattle that he gave to all visiting family, and likely everyone at the beach and all surrounding states. But we made it through, with the help of Shrek and Pedialyte and grandmothers. And while the smells of these horrors still seem to follow me around, I think I am stronger because of it.

In Miranda July’s first Substack post, she wrote that age is understanding that crisis and suffering is what actually makes you grow:

…that's one giant lesson of getting older, no? That without some kind of crisis that involves real suffering, it's hard to actually change, to see yourself and really approach life in a new way.

This is 1000% true for parenting, but I also think it relates to this month’s reader question: casual sex. Let’s get into it, and keep the questions coming in the new year.

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Is it actually possible to have casual sex? On the apps so many people write that 'casual' is what they're looking for, and while in theory it sounds great to have good communication and consistency all while keeping it casual, in reality I'm not sure thats possible. Thoughts?

- No strings, No problems?

I used to believe that for dating, suffering was part of the deal. That stretching the muscle and pushing yourself through the pain of bad dates and fuck boys would strengthen your core (values) enough to help you find the right one. Miranda July might agree, and maybe in theory, I did “make it out the other side” by getting married (if that’s the goal?). But I don’t know if online dating is what it used to be. In recent years I’ve been hearing about the trials and tribulations from friends on the apps, reading articles about dating app horror stories like this, singing along with Chappell Roan about it, and I’m starting to believe that this self-flagulation game of “casual dating” isn’t worth the payoff.

Hours and hours of in-app conversation that leads to nowhere despite the clear distinction in a profile that they aren’t here to “just talk and never meet up.” A person who hates being ghosted who then turns around and ghosts. A woman who just wants to have some casual attached sex, who keeps getting turned down for being too forward. Why is this so hard? Back in my day, online dating was exhausting and demeaning, but if you wanted to get laid and were willing to lower your standards and your morals, you usually could. Has the game been rigged, or are the players the problem?

Yes, the times have changed and the dating app burnout is real (the young people aren’t happy either), but for those I talked to (aka everyone over 30), casual dating is just not realistic like it once was. If you were on the apps back then and you’re on the apps now, you’re like a veteran solider with PTSD, running towards the thing that hurt you. If you are newly single looking to mingle, the clientele is just too jaded to even commit to casual sex. All those fish in the sea we were once promised are now either overfished or thrown back one too many times with flashbacks of their own. It’s depressing. Sure, we’ve all gotten older and rightfully more bitter, but I never thought casual dating in your 30s in 2024 would be as dismal as it was for the Sex and the City girls in 2004. Samantha being the exception, of course, she always seemed to enjoy the game and still does.

To get more insight, I looked through a list of hookups I had through my 20s. I started the Hit List years ago on my notes app for fun with friends, but it’s become a sort of time capsule of an era, a great end of the year activity to take note of how things have changed drastically.

For some reason I used code names and emojis to classify each fuck, so now, years after the events, the list has become a relic of characters, a disembodied experience classified by peach emojis (they made me cum) or skulls (toxic) or magicians (top hat). “Unfortunate Goatee” or “Asexual Clown in a Blizzard“ - these hookup tales are in my repertoire of party stories, but I couldn’t remember their real names if I tried. Obviously others held more weight, classified by the explosion emoji (there was a connection) or a range of hearts (there was love). My now husband is even on there with a growing number of icons (first came 💗 then came 💍, and now I just added a 👶).

Real names have been redacted for the safety of my exes from my exes

This year looking at my Hit List I realized: I’ve been fucking for twenty years. Sure, sometimes it’s been stretches of the same person or a dry spell of no one, but after two decades of getting down, you’d think I’d have more answers. The list as a whole (as are most things that you look back on in hindsight), makes my sex life look casual – cool even. Nameless notches on the belt. People remembered only by 🍑🍍☔️ (they made me cum but I was sad, and maybe on vacation?) The thing is, despite always trying to be a Samantha, I was never casual in the moment, no matter how hard I tried to be the cool girl with the list of lays in her pocket. I always wanted more: a consistent hookup, a boyfriend, to just be desired and wanted by SOMEONE beyond a night or two. I wouldn’t admit it then, but I think I was always secretly hoping for a nickname to turn into a 💗💍👶.

The one good thing about aging is the ability to more clearly see and define your desires. Whether it’s life experience or suffering that molds us, by our 30s we at least know what we don’t want. So, what do you actually want out of this dream casual hookup, No Strings? Of course a 🍑 fling like we had in our youth sounds great - a temporary lobotomy fuckfest without all the baggage of yore smackin’ around. But casual often comes with ☔️ or 💀 if what you actually crave in consistency and connection (which it sounds like you do). Twenty years of having sex and all I really know is I should have always just asked for what I wanted. We all play the “keeping it casual” cool card, but for me it was always just a protective way of holding my cards close to the vest, so there was no potential to get hurt again. So, No Strings, is casual sex actually what you want or would you maybe like to be strung up, if only a bit?

My task for you is to make a list of everyone you’ve ever smashed (emojis are optional, but highly recommended), and then look back and assess where you are right here, right now. Put judgements aside and ditch the “cool girl” jacket - what are you really looking for? Think of it as a New Year’s Resolution list but for the bedroom. Now ask for what you want: put it in your app profile, tell it your friends so they can be your wingmen and hold you accountable, say it out loud on dates. Manifest your mojo for 2025. Because “casual” isn’t really criteria on its own; it’s all the other adjectives that will make life memorable.

To celebrate twenty years of me hooking up, and a very prosperous and sexy New Year even in a trash world, here’s a menu from Vinegar Hill House’s Apocalypse themed New Year’s Eve dinner, the restaurant I used to work at during my most casual hookup days. This NYE, gather your friends, get a table at a banging restaurant like VHH (they still have reservations open!) or cook any of my past recipes at home, and share your Hit Lists over champagne as the clock strikes midnight. Cheers to knowing what you don’t want, and getting one step closer to knowing what you do. And remember, even in 2012 we thought we were living in the Apocalypse, so hindsight truly is 2020(5).