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Language:
English
Series:
Part 74 of May Tropes Mayhem , Part 2 of The Bachelor: Heaven
Collections:
May Trope Mayhem 2025
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Published:
2025-05-03
Updated:
2025-05-03
Words:
1,179
Chapters:
1/?
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5
Kudos:
8
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2
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59

Insider Information For the Win

Summary:

Sam got out of his season of The Bachelor: Heaven by already being in love with one of the constestants from the beginning. Dean had no such luck.

Notes:

Written for May Trope Mayhem 2025
Day 2: Bachelor Auction

Chapter Text

“So…” Dean stared at the twenty-four boxes on the table. “I get that I’m on The Bachelor: Heaven. What the hell is this all about?”

“For the first round, we are having a competition to determine which candidates are assigned to which date. A sort of bachelor auction, if you will,” Joshua “explained,” probably thinking he was making way more sense than he was. “Each candidate was asked to select a small gift, a token that would show that they know what is important to you and are willing to accept you for who you are. The joke of asking to borrow Sam to wrap up and put in their box was made approximately twelve times.” Sam turned away, snickering, and Dean glared at his back. Just because he’d managed to escape his own version of this bullshit, he thought he got to mock Dean’s struggles?

“The gifts are not anything particularly valuable, and may be things you already have. For example, I know that one of these boxes contains a cassette tape of Zeppelin IV. The idea was to show that they knew you, not to provide something of value, and I encourage you to make your decisions with that in mind.” He indicated the table to Dean’s right, which was divided into four unequal sections – the two end sections were both tiny, one of the middle sections was somewhat bigger but still small and was labeled 4, and the other middle section was huge. “From front to back, you have a section for the winner, who gets a one-on-one date with you, the honorable mentions who get a small group date, the ones that get the large group date, and then at the end is for anyone who failed the assignment so badly you don’t see the point in them continuing in this competition.”

Huh. Alex and Jody had explained how the dates were usually structured, and this sounded about right. “How do I know who gave me what?”

“You don’t, not until you’ve finalized your selections.” Great. There were probably gonna be hurt feelings here. Who thought these shows were a good idea? “There were going to be hurt feelings either way, Dean. This minimizes any accusation that you’re showing favoritism toward or against anyone.”

Fine. Dean reached for a box and opened it. This was in fact the Zeppelin IV. “Am I allowed to move them after I pick?”

“Of course, since there can only be one in the one-on-one and four on the small-group. No sense in locking you into something just because you opened things in the wrong order.”

Dean put the tape in the small date section. Not something that blew him away to the point of thinking this was the one, but still, pretty damn good. The next box had Slaughterhouse Five. Not bad, either, but he dropped this one in the large group date. The cherry pie in the next box originally went to the small group, but after opening two more right afterward, he decided all three belonged in the big group instead. The angel-themed porn magazine had to be Gabriel, right? Small group for sure, just for being hilarious, and a strong contender for the one-on-one. The next three boxes contained beer, which went straight to the large group. After all, he’d been trying to cut back thanks to Sam’s worry about him taking too much after their dad.

The mixtape was amazing. That had taken way more work than just conjuring up something, because the songs on the mixtape were all of Dean’s favorites. This was definitely going in the one-on-one unless it got knocked out by something better. The black paint confused him momentarily, until he looked at the name and realized it was the original color used by Chevrolet back in 1967. As often as he had to repaint Baby, this was a great gift. A Busty Asian Beauties, which got bonus points for being his favorite magazine. More pies.

The leather jacket was nice, although it missed the point that his favorite leather jacket had been his dad’s. The book about different types of werewolves and werewolf-like creatures had him just staring in disbelief. “Someone forget they’re on my season, not yours?” he joked as he held up the book to show Sam.

“Could be, or they could have been trying to invoke hunting, although for you a gun would’ve made more sense,” Sam said. “You gonna kick them out over it, or just chuck them into the large group date?”

Dean glanced down at the book. “Do I have to kick anyone out, Josh?”

“No. The option is there if someone gave you something so offensive or inappropriate that you don’t want to give them the chance to redeem themself, but it is at your discretion.” Joshua cleared his throat. “You should be aware that one contestant has challenged another’s right to be here.”

“Oh, here we go.” Dean rolled his eyes. “Someone here ‘not for the right reasons’?” Alex had warned him about this common drama thread.

“Yes. Specifically, there is a bit of unrelated drama that Hannah believes Miriam is using this as a pretext to leave Heaven to investigate, since all dates will be happening on Earth. It’s quite a long story, but she believes that Miriam is not here for you at all.”

Dean rolled his eyes. “Fair enough. I barely even remember who Miriam is, don’t really care what her reasons for being here are as long as she doesn’t fake too hard when it comes to staying in long enough to accomplish her goal.”

He went back to the boxes, dropping the wolf book in the large date pile. Whoever that was, it wasn’t bad enough to make him kick them out. The next box, though, this just might be. Who the hell thought it was a good idea to give him the book Chuck wrote about him being ripped apart by Hellhounds in front of Sam? Some more beer, four bacon cheeseburgers, and two pies later, he was at the last box.

“Thought you said these weren’t supposed to be valuable or big or anything,” Dean said, staring at the guitar that angelic dimensional woo-woo had managed to fit inside. “What the heck?”

“Keep in mind that all of the contestants are angels,” Joshua retorted dryly. “To an angel, that guitar is no more or less valuable than a can of beer.”

It was no surprise when Dean played a chord and it sounded perfectly in tune. It was between this and the mixtape for the one-on-one, with the other one taking the last slot in the small group date, joining the angel porn, black paint, and Zeppelin IV. The guitar required digging a lot deeper into Dean’s psyche, but the mixtape required more effort to put together. The effort won out. “All right. Think we’re done here.”

“Very well. I will let the contestants know that the small group date will be Anna, Michael, Rachel, and Gabriel, with Hannah eliminated and Gadreel winning the one-on-one.”

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