Dating While Grieving: The Messiest, Realest Thing I’ve Ever Done

The first time I tried to get back on Hinge after my brother died, I was still ugly crying. Like full-body, can’t-breathe, puffy-eyed crying. My phone buzzed, and I genuinely expected it to be some cosmic sign, a message from the universe, a reminder that I’m not alone.

It was a guy named Tyler who opened with:‍

“Heyy :) u up?”‍

Sir.
I am mourning.

This is what no one tells you about grief: the world doesn’t stop. Not even a little. Not for your heartbreak, not for your family, not for your sanity. And definitely not for dating apps.

Modern dating is already a circus. Try doing it while grieving someone who was literally your whole heart. It’s like grief hands you a new pair of glasses, and suddenly you can see every red flag from space.

Grief Gave Me X-Ray Vision for Bullshit

Before my brother died, I tolerated a lot. Late replies. Half plans. The classic “I’m just not ready for a relationship, but also please give me all your emotional availability” man.

After?
Absolutely not.

My tolerance for nonsense evaporated. I don’t want a man who “communicates sometimes.” I need someone who knows how to hold space for feelings—actual feelings, not just “work was crazy lol.”

Being emotionally intelligent went from “cute” to “non-negotiable.”
Consistency? Sexy.
Honesty? Sexy.
A man who doesn’t disappear mid-conversation? Pornographic.

I don’t have time to date boys. I barely have time to process my own feelings. If someone wants to be in my life, they need to show up like a grown-up.

Dating Apps While Grieving Should Count as a Sport

There is nothing more humbling than trying to choose a flirty bio while simultaneously spiraling about your brother’s memorial playlist.

Suddenly, the selfies I took “before” feel like flashbacks. I stare at myself thinking, wow, she had no idea. Meanwhile, the men on these apps are bragging about their Spotify Wrapped and how their personality is “go with the flow.”

It’s jarring.

Grief makes you crave depth. Dating apps make you scroll past guys holding fish. The cognitive dissonance is WHIPLASH.

I’m swiping with a grief brain. I’m answering “What are you looking for?” with “Someone who won’t crumble when I inevitably cry in a parking lot,” which feels like too much honesty for an app whose main export is emotional avoidance.

It’s Basically a Three-Way Date (Me, Him, and My Brother’s Energy)

Every time I go on a date now, my brother is with me. Not in a sad way — in a “he shaped me” way.

I automatically think:
Would my brother have roasted this man?
Would he have liked him?
Would he have given me the eyebrow raise of doom?
Would he have said, “Sam, this is NOT your man,” or “Okay, queen, yes, date him”?

Grief turns your intuition into a superpower. You hear your person’s voice louder. You trust your gut more fiercely. And you stop settling for people who don’t match the emotional depth you’re living in.

Hookup Culture Feels… Different Now

I used to think hookup culture was disappointing. Now I think it’s borderline absurd.

Like, we’re all out here trading half-hearted situationships when literally anyone could lose someone tomorrow. How are we prioritizing “vibes” over actual connection? How is “what are we?” still considered clingy in a world where tomorrow isn’t promised?

Grief makes you bold.
It makes you crave meaning.
It makes you allergic to bare-minimum effort.

If modern dating is a minefield, grief turns it into a neon-lit obstacle course where every inconsistency or lack of emotional depth flashes like a warning sign.

Grief Made Me Softer AND Scarier

Here’s the twist: losing my brother didn’t make me closed off. It made me softer… but also a little terrifying.

I love harder.
I feel deeper.
But I don’t tolerate shit.

I know what matters now. I know who I am. I know the version of myself my brother loved, and that’s the version I want to bring into every connection.

Grief didn’t break me.
It refined me.
It raised my standards.
It made me crave a love that feels like someone saying, “I’m here, even in your darkest moments.”

So Why Am I Still Dating?

Because my brother would want me to.
Because love still matters.
Because I’m still here.
Because grief didn’t take away my desire — it just made it more intentional.

Dating while grieving is messy and confusing and sometimes hilarious in a “wow this cannot be my life” way. But it’s also honest. And vulnerable. And real in a way modern dating desperately needs.

I’m not looking for someone to fix me.
I’m looking for someone who can sit with me in the dark, laugh with me in the chaos, and choose me in the reality—not the curated highlights.

If someone can hold that?
They’ll get a version of me who’s braver, deeper, more loving, and more alive than I’ve ever been.

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