BeautifulCalamity57
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Prompt #24: You’re my ex but I think I still have feelings for you
From this prompt list
For princessjimmynovak! This was requested approximately a million years ago and I finally finished it!! Happy belated birthday darling 💜
Feat. Space Ex-Boyfriends who are bad at talking to each other. So canon. But in space. (Dean has always wanted to be an astronaut, lbr)
Bookmarked by BeautifulCalamity57
22 Feb 2026
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Castiel ends his relationship with Dean when he can no longer stand what they’ve become—two people circling the ghost of something they once cherished. Yet, despite the break, his love for Dean doesn’t fade. When Castiel returns to Dean’s apartment to gather the last of his things, he stumbles upon a folder of unsent emails—every one of them addressed to him.
As he reads, he discovers the truth Dean never had the courage to say aloud: that he loved Castiel deeply but never knew how to put those feelings into words.
**
Draft #18 — October 9, 2025
Subject: the night you left
Cas,
I didn’t sleep after you left. I sat on the floor until the light came up.
The space where your things were looks too big now. Empty in the wrong way.
I keep hearing your footsteps, even though I know they’re not there,
It’s funny—how quiet used to mean peace. Now it just means you’re gone
If you never come back, I want you to know this:
You were the best thing I ever had the guts to ruin.**
Each message is a confession written and deleted a hundred times, a silent record of everything Dean felt but couldn’t express until it was too late.
Bookmarked by BeautifulCalamity57
22 Feb 2026
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… In which Castiel confesses but he can’t bear the look of disbelief on Dean’s face (and dreads his answer too much) so he makes Dean forget.
Over and over again.
Bookmarked by BeautifulCalamity57
16 Feb 2026
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Team Free Will throws a low-stakes Halloween party in the Bunker, streamers, plastic bones, and Jack in a DIY ghost sheet. Sam shows up as a vampire. Bobby brings beer. Charlie won’t stop stirring the pot. And Cas? He walks in wearing Dean’s uniform: flannel, denim, boots, looking like he raided Dean’s closet on purpose.
The jokes start. Dean bolts for “air.” In the quiet corridor, one truth becomes impossible to dodge. Confession turns to a hallway kiss; a messy, perfect first time follows, praise, filth, and years of wanting finally burning off, before soft aftercare and a private moment where angels don’t sleep… but they do stay.
Bookmarked by BeautifulCalamity57
06 Feb 2026
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Sam and Jess are getting married and Dean couldn’t be any happier for them. Honestly, they’re kind of disgustingly perfect for each other and Dean’s pretty damn excited about staying with them the week before the wedding. He’s Sam’s best man, of course, and he doesn’t even mind that Jess has her own best man to share in all the organisational duties. The more the merrier, right?
Except Dean must have done something to epically piss off the universe because Jess’s best man just happens to be Castiel friggin’ Novak. He’s got even hotter since High School, but apparently no friendlier and if Cas wants to spend the week pretending like they’ve never met before? Fine. Two can play at that game.
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Bookmarked by BeautifulCalamity57
25 Jan 2026