How to Lose a Guy in Two Days

On casual relationships

Last week I crashed out over a skater boy . . . twice.

The first time it happened, I was at a friend’s birthday party, re-applying my lip liner in the bathroom. He texted me back (I had sent a wyd tn text a couple of hours before), saying that he was working on a playlist to send me. My ears perked up. I waited exactly ten minutes before replying.

When he didn’t respond, I found myself standing outside 7/11 at midnight, smoking a skinny cigarette, annoyed and staring at my phone. I voice noted a friend who said:

Girl go to bed lol

Begrudgingly I trudged home, blasting Barbie Dreams in my earbuds.

This was a minor crash out. Nothing particularly embarrassing happened, I just Wanted It too much, in a way that froze my sense of agency. I had hook-up tunnel vision and I was irritated myself.

The second time it happened was much, much worse. After sleeping through a booty call text the night before, I sent a “chill” and “casual” message back (sorry I was sleeping.. But I’d love to see u tn). He said he’d let me know when he was around later.

Four margaritas and zero texts back later, I called him. He hung up on the third ring and I sobbed, sobbed, on the walk home, crying to my cousin Kira over the phone.

“Oh baby,” she said. “It’s okay.”

“I’MSOEMBARASSED” I wailed, clomping down the street in my knee high boots.

“It’s not embarrassing to call, it’s just a hook up!” she replied.

This is what I like to call the point of no return — when the car goes over the cliff, when the house burns down. Ultimately, this sort of crash out isn’t actually about the other person, it’s about how I’ve let the relational dynamic impact my sense of agency (Jesus take the wheel). It occurs at a specific point on the Casual Sex Axis, where the lines between Fun and Worth It and Stressful and Not Worth It merge.

In the past, I’ve lost myself in situations that should have just been casual hook ups. Craving a deeper connection from the wrong person, my Wanting sent them running in the other direction (and me after them).

When I realized that I was projecting this Wanting (my core desire for a healthy, loving relationship) onto a skater boy who only texts me from 11 pm to 2 am, alarm bells went off in my mind. The car squeaked to a halt at the edge of the cliff as I slammed on the brakes.

On TikTok, there’s an oft-quoted line that goes something like: “When you’re obsessing over a man, you’ve abandoned your creativity.”

Prior to meeting said skater boy, I was firmly in my vibe: constantly thinking about my next essay, walking down the street writing paragraphs in my notes app, visualizing my dream life in bed in the morning. Post skater boy hook up, I drifted further and further from this place of healthy self involvement. In the mornings, I reached for my phone first (which makes me feel like shit), checking for his inevitable 2 am text back, crafting a witty, yet cute, yet succinct response with my sleep mask still wrapped around my bedhead. This sort of toxic behaviour accumulated (compulsive phone checking, going out late in hopes of getting hit up later), leading to my eventual margarita-fueled crash out.

I was texting with my friend who’s a therapist the morning after, curled up on the couch post scalding hot shower, cradling a cup of coffee.

It’s ok I get it, I’ve been there. He’s probably been there too, she said.

But your desire for this guy who doesn’t matter is way too high. It shouldn’t go past a 3 like, ever lol.

Here, I thought about the different types of relationships that fall under the Casual Sex umbrella: situationships (kill me), friends with benefits (friends with benefits isn’t fun, bc you aren’t really friends, and there aren’t really any benefits my therapist friend texted me) and casual dating.

It’s my mathematical understanding of the equation that the most devastating, ending-of-Thelma-and-Louise style crash outs occur in situationships, as a situationship is another term for Being Delusional And Lusting After Someone Who Clearly Does Not Like You And Definitely Does Not Like Themselves. Situationships are often (always?) harmful to your sense of self, as they provide excellent material for every insecurity, neuroses and attachment issue to latch onto and feed off of for months or — in critical cases — years. In my experience, I only get into situationships when I’m bored, craving chaos and drama to distract me from the fact that I’m dissatisfied with my life (happy to report that I haven’t had one in a while).

Friends with benefits, in my limited experience of this type of no-strings-attached relationship, follows a formulaic timeline: you meet, flirt, have sex and proceed to text every day with no concrete plan to hang again, knowing that try as you might (wyd tn), they’ll hit you back on a random Wednesday in three weeks asking if you want to come over rn? This is how I would categorize the skater boy dynamic, and what I can deduce from the life cycle of that relationship is that the point where it stops being fun and starts being more time and energy draining than it’s worth occurs very early on.

This brings us to casual dating. Dating apps, drinks, etc. This category is tricky: while friends with benefits can be skaters or bartenders or both, and situationships can be anyone who makes your nervous system go into a state of permanent shock, in my experience I only casually date people I would potentially get into a relationship with. Ergo, sex means something different here — the stakes are higher.

Over 11 pm glasses of red with a friend, at a tiny French diner on a sleepy Sunday, the topic of what constitutes casual sex came up.

“I only have casual sex when there’s a clear reason why I cannot date the person,” my friend said. “Like they’re only in town for a week, for example.”

I mulled this over as I sipped my wine, concluding that this is is what gets me into trouble on both sides of the equation: having casual sex with serious contenders who don’t take me seriously, and having casual sex with unserious contenders who I take too seriously. It’s a hook up culture ouroboros loop!

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In How to Lose a Guy in Ten Days, Kate Hudson’s wry New York columnist Andy Anderson attempts to drive away Matthew McConaughey’s charming and conniving aspiring diamond salesman Benjamin Barry. The plan is simple: Andy’s writing a column about how to lose a guy in a week and a half, and Ben is trying to prove to his eccentric boss that, by making a woman fall in love with him, he can sell diamond jewellery.

When I rewatched the movie recently on my laptop in bed, I shuddered when Andy’s sardonic friend jokes that she should “call him in the middle of the night and tell him everything [she] ate that day,” while her earnest, Crash Out Princess counterpart Michelle (played by Kathryn Hahn) asks, baffled, “what’s wrong with that?”

This scene makes me think about what we’re not taught as women when it comes to dating men. On the flip side of the “if he wanted to he would” coin is the notion that, if a guy is really into you, you should be able to do whatever you want, and it shouldn’t matter. I remember the millennial TikToker Tinx once describing how she threw up on her ex boyfriend’s shoes before they started dating, and how he still called her the next day.

“You’re so pretty Andy, you could barf all over a guy and he would say do it again,” Michelle quips.

“That is flattering and ultimately so untrue,” Andy retorts. “If the most beautiful woman in the world acted the way you did, any sane guy would go running in the other direction.” Here, she’s referring to Michelle’s tendency to cry after having casual sex and to say “I love you” after two weeks because she wanted to “express herself.”

It’s critical to remember that Ben only puts up with Andy’s behaviour (which, with a different movie score, could watch more like Fatal Attraction than a romcom) because he’s trying to win a bet at work. And that when he does eventually fall for her, it’s because she embodies the cool girl elements that Amy Dunn listed in her iconic Gone Girl monologue — she’s aloof, she treats dating like a man, she’s sharp and discerning. Andy as her non cosplaying-a-girl-who-guys-consider-crazy self plays the dating game similarly to Charlotte York in Sex and the City. She avoids sex on the first date to gain his respect, she’s focused on her career and she isn’t seeking a relationship to fill a void.

At the French diner with my friend, we talked about the difference between playing the game and having game.

“It’s not about changing anything about who you are, it’s about shifting your priorities and having boundaries,” she said, in regards to healthy dating. Here, I think about how there’s power in understanding the nature of a dynamic, and deciding whether or not it’s worth playing out.

When I woke up the morning after my crash out, in the back of my mind I felt relief. The cord had been cut, I was free. When my therapist friend suggested that I write about the experience, and the conversation surrounding casual dating that she and I were discussing at length, I felt a switch turn on inside of me — a creative spark that had laid dormant during my three week post sex haze.

I feel my best when my brain space, which I cultivate like a garden, with gratitude and visualization and creative inspiration, is protected, kept sacred and stimulated. By meditating on future dreams and writing essays, making playlists and drawing birthday cards. Running and cooking and reading. Going out for dinner with friends. Not waiting for a text back.