on balancing detachment + connection

how i learned to care without caring too much

I had a major crush on this guy for months. I was a bartender, he was a regular. Charming, tall, dark, handsome, successful, ten years older than I was. He'd always pay with his thick, platinum Amex that made my minimum-payment-struggling credit card look like a library card. 50% tip at minimum, sometimes 100% depending on how many tequila sodas I served him.

We’ll call him Caleb.

At the ripe age of 25, I was probably the most insecure I’d ever been, but for those 8 or so hours I was behind the bar for my shift, I was able to develop a false sense of confidence. Put a giant boot of Miller Lite in my hand and suddenly I had power — a young, cute girl calling the shots for a bunch of grown-up frat bros whose biggest concern was whether they could see the Clemson game from their barstool.

In a sea of backward hats and jerseys (Alpha Delta Whatever, ick), Caleb stood out like a beacon of actual adulthood. He'd arrive well-dressed, make eye contact when he spoke, listen when I answered, and did I mention he was hot asf?? 😭 He made me feel seen in a way that had nothing to do with my ability to pour drinks. That Saturday shift energy became my weekly hit of validation. He'd walk in with friends but spend the entire time talking to me, making me feel like I was somehow the most interesting person in a room designed for distraction.

“So are you f*cking this guy or what?” my coworker asked.

“Shut up!!! No!!” I blushed. Ugh I wish.

This tension had built up for months. Incessant flirting, overtipping, “I missed you last week, did you take last Saturday off?”s.

Then one day, it happened.

The bar I worked at didn’t print paper receipts. You tipped and signed your bill directly on the iPad.

I handed Caleb the iPad to close out his tab, he gently took it from my hands and asked if I could print the receipt for him.

“I need somewhere to write my number down because it’s about time that I took you out.”

adadasodjajsfjofjhs;ohe!!ssirjshnf!!!! j#@#$@~!! (literally me)

My insides were screaming, but I did my best to play it cool.

“Oh? And what if I’m busy?”

“Then we’ll pick a day when you’re not.”

My coworker overheard this interaction (the same one that asked if we were f*cking a few weeks prior) and immediately shot a look at me. You know the exact look I’m talking about.

“What?????”

“Oh nothing, Beth. Oh, nothing.”

My upcoming date with Caleb consumed my brain 24/7. Ofc I did my proper social media stalking (ten times a day) and envisioned our future together as any naïve and insecure 25 year old girl does when she gets even a crumb of attention from a man.

Fast forward to our date.

He took me to a fancy wine bar downtown. Glasses of wine were drunk, words were slurred, a time was had.

The date itself was a blur of expensive wine and fun conversation. I remember laughing at all the right moments, feeling special when he ordered another bottle without glancing at the price, and trying desperately to be the cool, effortless girl I thought he wanted.

We ended up back at his place — the penthouse of a luxury apartment complex, of course.

I woke up the next morning to sunlight streaming through floor-to-ceiling windows, momentarily confused before remembering where I was. Caleb's 1500-thread-count sheets (or whatever ridiculous number rich people use) felt impossibly soft against my skin. For a split second, I let myself believe this was the beginning of something real. That maybeeee this was how my love story started (ugh, to be young and stupid again lol).

And then came the shift.

"Hey, you're up," he said, already dressed in workout clothes, keys in hand. "I've got a training session at 9. There's coffee in the kitchen if you want some."

His tone wasn't mean. It wasn't cold. It was just... indifferent. Like I was an Amazon package that had been delivered and acknowledged but wasn't particularly exciting.

No "last night was amazing." No kiss on the forehead. No "when can I see you again?" Just the casual expectation that I'd be gone by the time he got back.

I mumbled something about needing to get home anyway, gathering my clothes while trying to maintain whatever dignity I had left. The walk of shame feeling hit differently when you weren't just leaving a random hookup but exiting what you thought might be the prologue to your future.

"Text me," he said as I left, in that way people say when they absolutely do not want you to text them.

I spent the next week checking my phone like it was hooked up to life support. Dissecting every moment of the night, wondering what I'd done wrong. Was I too eager? Not interesting enough? Did I say something stupid after that third glass of wine?

The worst part wasn't even the rejection. It was realizing that the version of Caleb I'd built up in my head for months — the one who saw me as more than just the girl behind the bar— was never real. He was just a guy who wanted what most guys want, and I was just another bartender he'd successfully charmed.

I saw him at the bar two weeks later with another woman. He tipped 100%.

Was he a bad guy? No. At the time did I think he was a total fuck boy? Yes. But I was also 25, naïve, and like I said, salivated at the mouth for any guy that gave me the tiniest crumb of attention.

Despite all of that, I was hurt. I felt used, gross, and stupid.

But it wasn’t just about Caleb. It was the guy before him too, and the one before that.

…and the people that came after him too.

I'd build these people up in my head, spinning elaborate fantasies while simultaneously trying to be the "cool chill girl" who didn't care. But spoiler alert!!!! I wasn't cool or chill at all (shocker). I was a mess of anxiety and insecurity, measuring my entire self-worth through other people's reactions and desires to me.

I told myself that casual sex was just something liberated, modern women did - so it was "no biggie" to me. I could totally handle it...until I realized that "casual" was all I ever was to them.

Just casual. Never someone worth actually getting to know.

So I leaned into it harder. More hookups, more partners, plummeting self-worth. It became this twisted cycle - using physical connection as a substitute for what I really craved: genuine connection. When your self-esteem is in the gutter, that feeling of being wanted, even temporarily, becomes addictive. Even when it leaves you feeling emptier afterward.

The more I tried to armor myself—pretending I didn't care, expecting the ghosting before it happened—the more it hurt when it came. My attempts at emotional detachment only made me more vulnerable to the rejection that always followed.

That was what I like to call Hoe Phase 1. Sounds fun, right?

Let's fast forward to Hoe Phase 2.

Oh hey! It's me at 32, navigating what I've come to call Hoe Phase 2. Except this version looks nothing like its predecessor. This time, I actually am that liberated woman who can do casual without the emotional hangover. I still get emotional hangovers, just not about dating lol

The difference? It's not about sex or validation or filling some void or the men or the women or the general woes of modern dating. It's not about any of that.

Phase 2 exists because I finally got tired of my own bullshit. I got tired of checking my phone every five minutes, tired of the mental gymnastics, tired of making excuses for people who couldn't even be bothered to text back.

I made a promise to myself: I would no longer put my emotional stock in people who haven't earned it. I would enjoy the moment for what it is – not for what I hope it might become. I stopped chasing and started matching energies instead.

It’s called the law of detachment, and it’s completely transformed my relationship to dating.

I stumbled upon this concept on TikTok (duh). As an anxious attachment lovergirl girly, the idea of simply ~letting go~ of any potential outcomes or expectations seemed..crazy? Impossible? Idk.

When I started being fed this kind of content back in the fall I just dismissed it at first.

It was New Year’s Day and I woke up hangover free in my little tiny cabin on the Finger Lakes in upstate New York. The snow had just started to fall, I knew I needed to leave sooner rather than later to make it back to Chicago before the weather got any worse.

But before I left, I knew I wanted to align with myself on a few intentional resolutions, and more importantly, my Word of the Year.

Think what you want about New Years, but I always appreciate a metaphorical clean slate or whatever you wanna call it.

I sat there on the porch as Kevin zoomied around in the front yard and reflected on last year's New Year's Eve. I was in a relationship at the time, and I can’t remember what we got into an argument about, but I do remember that I still had tears rolling down my face as the Time Square ball was dropping on the TV in front of me.

I let out a deep breath and continued to scribble in my journal.

I landed on two specific resolutions, which then led me to my Word of the Year.

1. Decenter men

2. Practice the law of detachment

Based on these two resolutions, “detachment” felt like the one. It felt like the Word.

I shut my journal, packed the car up and headed back to Chicago.

So when it comes to dating, what exactly does detachment look like? I’ll tell ya.

Detachment isn't about becoming emotionally numb. That would quite literally be impossible for my Pisces, overly empathetic ass 😭. It's about caring differently. It's taking the person exactly as they are in that moment without mentally fast-forwarding to some future or outcome that only exists in your brain.

Detachment means understanding that you can't predict or force what happens between two people - you can only control how you show up.

It's enjoying a witty conversation over drinks without immediately wondering if they'd make a good "+1" at your cousin's wedding. It's about having great sex without immediately planning breakfast the next morning. It's texting when you want to, not because you're strategically waiting the "right" amount of time.

Detachment is recognizing that someone can be a perfectly nice person and still not be your person. That someone can be fun to hang out with on Tuesdays but not necessarily boyfriend material. That initial chemistry doesn't equal long-term compatibility. It also means seeing people exactly as they are—not making excuses for red flags or bad behavior just because you're attracted to them.

When you stop obsessing over the outcome, you give yourself the freedom to just…be. And that, my friends, is freeing as fuck 😭. By releasing expectations from yourself and other people, you prepare yourself to face whatever outcome comes your way. You trust the process rather than trying to force and control it.

Most importantly, detachment is understanding that your worth isn't tied to whether they call or text you back. That their behavior says more about them than it does about you. That you're the constant in your life - they're just variables passing through.

It's taken me 32 years and countless therapy sessions to realize that I can actually enjoy dating when I'm not treating every match like an audition for the role of "person who calls me pretty, buys me flowers, and validates my existence.”

I’m tellinggggg you, matching someone else’s energy is FAR less exhausting, and way more fucking freeing than investing more of your own.

Am I still insecure? Yes lol. Do I still want someone to call me pretty and buy me flowers and all that corny bullshit? Yes. But I’m also not going to chase that energy or ask them twice. Thank u, next.

So, how’s detachment dating going?

Honestly, fan-fucking-tastic. No, really. Dating is way more fun this way.

First off, I’d be remiss not to say that the Chicago dating scene is 1000000x better than DC or Boston. Like, truly. Idk if it’s the Midwest niceness, or just the fact that I’m in my 30s now and have a clearer idea of what I want and what I don’t want. Idk what it is. But, dating here is just so much better.

This doesn’t mean that all of the dates I’ve gone on have been great. There have definitely been a handful of mediocre dates, and one really bad one lol – but most have been a really positive experience, even if one or both of us agree that we aren’t interested in pursuing a 2nd date.

And that’s ok!!

I heard this podcast episode recently where this woman was talking about her dating experiences - how she'd go on these subpar dates with these subpar men, and then get upset when they'd ghost her or say they weren't interested.

But then she'd have this moment of clarity: "Wait, did I even have a good time on this date? I don't think I did. Why the fuck do I care if this man doesn't wanna see me again???"

I've never related to something more lol. It all ties back to ego and the desire to feel validated.

Ok so detachment dating, great awesome cool. But here’s the thing that's been screwing with my head: what happens when detachment actually works too well? When you meet someone who might actually be worth getting attached to?

That's the messy middle ground I'm trying to navigate now. Detachment has made me more confident, more myself. I'm no longer that 25 year old desperately seeking validation from a random guy with a decent smile and thick wallet. And honestly? It's working - I'm meeting better people, having better conversations, and actually enjoying dating for once.

But the unexpected challenge is figuring out when and how to scale back the detachment without completely abandoning it. How to recognize when someone might be worth letting in a bit closer than arm’s length.

Because here's what nobody mentions about practicing detachment - it gets complicated when you genuinely start to like someone. Suddenly all those rules I made for myself feel like they're in the way. The carefully constructed boundaries I've built start feeling less like protection and more like obstacles.

I find myself wondering: what does healthy attachment even look like? Is there a middle ground between the anxious overthinking of my 20s and the cool detachment of my 30s? Can I let someone see more of me without completely throwing away all the boundaries I've worked so hard to build?

I feel like I’ve explored both sides of the pendulum, but haven’t seen what the middle could look like.

Like I’m doing what my dad tried to drill into my head when teaching me to drive, “Drive defensively, Bethie!!!” I’m doing that. Driving defensively. But now I'm trying to figure out when it's safe to speed up a little. Not recklessly, not like before, but with the wisdom of someone who knows both the thrill of the gas pedal and the importance of the brake.

Damn I gotta fucking stop with the metaphors lol sorry

Because the point of all this dating isn't to be perpetually detached - it's to find someone worth attaching to, on my terms, in my time.

But actually, I take that back. That's not the main point. The point of practicing detachment theory, for me at least, is to build myself up. To stop giving so many fucks about what other people think or do. To remember that my life doesn't revolve around whoever I'm dating at the moment. It's about knowing that whatever happens in my dating life—good, bad, or ghosted—I'll be okay. I existed before them, I'll exist after them, and I'll keep doing my thing regardless of whether someone wants to stick around for it or not.

And plus, I got so much other shit to worry about rn that’s much more important than Luke on Tinder. Kim, there’s people that are dying!! Like, let’s be so fr😭

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thanks for reading,

b 🫶✨