I ruined three relationships by overthinking—here's what I wish I'd known sooner

I’ve spent most of my adult life trapped in my own head.
It sounds harmless enough—just someone who “thinks a lot.” But thinking and overthinking aren’t the same. One solves problems. The other invents them.

I learned that the hard way—through three breakups that could’ve been love stories if I hadn’t let my anxious brain narrate every moment.

1. The illusion of control

My first real relationship was with someone who taught me how warm life could be when you actually let another person in. She was spontaneous. She’d decide on a whim to drive to the coast or make dinner from whatever was in the fridge. I, meanwhile, was planning the future down to the next Tuesday.

When she didn’t text back for a few hours, I’d imagine the worst. If she seemed distracted at dinner, I’d replay the conversation a hundred times to see what I’d said wrong.
Overthinking gave me a false sense of control. I believed that if I could just figure it out, I could prevent pain.

But here’s what I wish I’d known: love doesn’t happen in your head. It happens in the messy, uncertain space between two people. Trying to control it is like trying to direct the tide.

I pushed her away with my constant need for reassurance. She said she felt like she was being “auditioned for love.” That phrase haunted me. Because she was right—I wasn’t loving her; I was constantly evaluating whether she still loved me.

2. Anxiety in disguise

If you’ve ever dated someone who overthinks, you know it doesn’t come from arrogance—it comes from fear. Fear of being misunderstood. Fear of losing something good. Fear of not being enough.

By the time I entered my second relationship, I thought I’d learned from the first. I promised myself I’d be “chill.” But overthinkers don’t get rid of anxiety—they just get better at disguising it.

I stopped asking questions out loud, but inside, I was still building mental spreadsheets of every text, every glance, every pause. My brain was a 24/7 analytics dashboard of imagined meanings.

I once spent an entire weekend wondering why she said “you’re funny” instead of “that’s funny.”
You read that right. Two days. Because “you’re funny” could mean “you’re funny… weird.”
It sounds ridiculous when I write it down—but that’s the nature of overthinking. It always feels rational in the moment.

I wish I’d known that peace in relationships doesn’t come from analyzing less—it comes from trusting more. Not because trust is easy, but because it’s the only antidote to the mental noise.

3. When love feels unsafe

By the third relationship, I thought I was becoming wiser.
I’d started writing about music and food—two subjects that let me focus on feeling instead of constant analysis. I found comfort in sensory things: the way a synth line shimmers through headphones, or how a batch of homemade kombucha hisses when it ferments. Those details made life feel real again.

But when I fell in love, all that mindfulness disappeared. Suddenly, my mind turned every quiet moment into a referendum on the relationship.

If she didn’t seem as excited to see me one night, I’d spiral: She’s pulling away. She’s realizing she can do better.

When you’re used to overthinking, calmness feels suspicious.
You don’t trust peace—you wait for the drop.

And so I kept self-sabotaging. I’d over-communicate to “fix” things that weren’t broken. I’d apologize for problems she hadn’t even noticed.
Eventually, she told me, “I feel like I’m always managing your emotions.”
And that was the moment it clicked: overthinking doesn’t just exhaust you. It exhausts the person who loves you.

4. The lesson from fermentation

There’s something poetic about fermentation. You mix ingredients, seal them up, and then—you do nothing. You wait.
You don’t poke it every few hours to make sure it’s working. You don’t micromanage the yeast. You trust the process.

That’s what I wish I’d done in love.

Because relationships, like fermentation, are a balance of control and surrender. Too much control kills growth. Too little, and it goes bad.
But when you give something just enough space—it thrives.

I’ve learned that the hardest part of love isn’t finding someone; it’s not letting your fear of losing them make you act like you already have.

5. The stories we tell ourselves

Overthinking is storytelling gone rogue.
You take a small event—like your partner glancing at their phone—and your brain writes a 10-episode psychological thriller. Each episode ends on a cliffhanger.

In reality, they were just checking the weather.

When I look back on those relationships, I see how much of my pain was self-created. I was constantly editing a movie in my head—cutting out the laughter, looping the arguments, color-correcting reality into something darker.

I wish I’d known how unreliable my own thoughts were when fear was the director.

What finally helped me see that was journaling.
Every time I caught myself spiraling, I’d write down what I knew versus what I imagined.
Example:

• Knew: She said she’s tired.

• Imagined: She’s tired of me.

Once you separate fact from fiction, overthinking loses some of its power. The stories fall apart under the weight of their own exaggeration.

6. How I finally started unlearning it

It didn’t happen overnight.
Overthinking is like muscle memory—you can’t just stop; you have to retrain. Here’s what worked for me:

a. Naming it – I started saying, “That’s my anxious brain talking.” Just that small distance between me and the thought changed everything. It reminded me I wasn’t my panic.

b. Returning to the body – I’d focus on something sensory: the taste of mint tea, the sound of rain, the smell of sautéing garlic. It anchored me to the moment instead of the mental maze.

c. Saying it out loud – I learned to tell my partner, “Hey, my brain’s spiraling a bit.” Most people are kinder than your inner critic. When you name the thought, it stops owning you.

d. Accepting ambiguity – This was the hardest. Real connection means letting some questions remain unanswered. You can’t spreadsheet your way to security. You build it, moment by moment, through honesty and patience.

7. The beauty of not knowing

These days, I write about culture and food. I spend time photographing things that don’t need to make sense—like the swirl of light on a rainy street, or a perfectly imperfect loaf of sourdough.

I’ve realized that the beauty in both art and love comes from imperfection. From the space where you stop forcing meaning and start letting things be.

When you stop overthinking, you start seeing people more clearly. You notice how someone’s eyes soften when they talk about their dog. You hear the warmth in a text that you’d once overanalyzed. You start trusting that love isn’t fragile—it’s just human.

8. What I wish I could tell my past self

If I could go back, I’d tell the version of me pacing his apartment at 2 a.m., checking his phone, dissecting every silence:

“Stop looking for evidence that you’re loved. Start noticing the ways you already are.”

Love isn’t a puzzle to solve; it’s a presence to experience.
It’s not about decoding hidden meanings—it’s about letting someone’s kindness, laughter, or even their flaws exist without turning them into data.

I’d tell him that silence doesn’t always mean distance. That reassurance can’t fill a hole only self-compassion can. That sometimes, the healthiest thing you can do is close the browser tab in your mind and just sit with what is.

9. The quiet after the storm

When my last relationship ended, I didn’t rush to fix myself.
I took long walks. I brewed tea. I listened to the same lo-fi playlist on repeat until the songs felt like home.

And somewhere in that quiet, I realized that the goal isn’t to stop thinking—it’s to think kindly.

You can still be introspective without being self-destructive. You can reflect without dissecting. You can care deeply without constantly checking if it’s safe to do so.

Overthinking doesn’t make you broken—it just means you care so much that your brain doesn’t know where to put it all.
But care needs air. It needs silence. It needs the kind of stillness where love can actually breathe.

10. Moving forward

I haven’t stopped overthinking entirely. I still have moments—usually when I really like someone—where I feel the old patterns stirring.
But now, when that happens, I remind myself of something simple:

Love doesn’t need a conclusion. It just needs attention.

That’s the paradox of overthinking: the more you try to understand love, the less you can feel it.

So these days, I let the music play. I taste the food before judging it. I let people surprise me.
Because maybe that’s what life—and love—are meant to be: not perfectly understood, but beautifully experienced.