You've sold your soul for a very slightly better handjob. Nowhere does the contract say it's mind-blowingly better.
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The devil has to go first so he won't know how much better to make it.
He's the devil.... Trust me, he'll know.
In my expirience i will always win unless the handjob is within 5-10 days of distance because every handjob after the first one is just not as good in that window of time
If he waits i can just do one every once in a while until he gets bored or i forget for more than 5-10 days
A philanthropism challenge. Improve the world the most. I'll lose, but whatever I do, he'll top it. And then it'll trigger the self sacrifice clause (which I can't know about beforehand) and I'll win anyway.
How do you measure this though?
Magic
Send us both to heaven. The last person to leave heaven loses.
So, you're both in heaven and the last person to leave loses, assuming you mean just out of the two of you (since this is about winning a competition against the devil), the devil would leave immediately and win. Are you assuming the devil can't then claim your soul since you're already in heaven? Why not just make it "the last one to leave wins" and then you and the devil are in a staying-in-heaven stalemate.
I'm pretty sure they meant first one to leave loses (or last one to leave wins) and just had a brain fart.
Bro, what if heaven sucks shit?
I'd challenge him to a "not in any way actually being the devil" contest. The only way in which he could win is if he made me the devil and him not actually the devil and as soon as he did it I'd harvest his soul and move on with my new infinity power.
He's a magical being. Any competition is pointless, you'll lose. It's just another way to torture people.
I'd refuse. What's he going to do? Torture me?
The old story/song, "The Devil Went Down to Georgia," isn't about a young man winning a bet against the Devil that he's a better fiddle player. It's the devil tricking poor Johnny into the sins of pride and greed.
The Devil pretended to lose so that Johnny would think that he was the best fiddle player in the world, even better than the all-powerful devil himself. (Pride) And then Johnny claims a reward of a solid-gold fiddle. (Greed) Johnny just cursed his soul to damnation, thinking he could actually beat the devil at his own game. It was a no-win scenario; the devil claims his soul either way.
It was a no-win scenario
Johnny could have just said "Beat it, dipshit." When the devil offered him a bet.
Yrah, he could have said "beat it, just beat it."
Isn’t that what OP is proposing?
This is emphasized in the song by the fact that the Devil's fiddling is way better than Johnny's.
Well the fucker cheated (surprise surprise) by having a band of demons join in.
That was just for flair. The isolated fiddle part was better alone anyway
Arguably wrath too ("I done told you once, you son of a bitch"). Also, isn't God the only thing you could reasonably call the Devil's parent? Did Johnny call God a bitch?
People may say, "Well Charlie Daniels beat him."
Charlie Daniels is also a magical creature.
So is Les Claypool. (Primus covered it)
The dumbest thing he could do is appear and offer a deal.
If He exists, than so does God, so it makes sense to be good, because you know it's worth it in the end.
Which gives a different slant to the saying 'the best trick the Devil ever pulled was making people stop believing in Him.'
I challenge the devil to end world hunger forever. First one to feed the world wins.
I suppose there could be some monkey paw-esque shenanigans killing billions, but at this point we might as well let a non-human cosmic being do it.
If he feeds everyone great, if he kills a ton of people at least the climate crisis is sorted and thousands if not millions of animal species are saved. I avoid the moral implications since the intent was to feed people and the devil picked the evilnest option. But honestly I think they would just solve world hunger a more normal way.
Apparently his fiddle game is trash, or so I hear.

Devil never said solid gold, so it probably wouldn't sound much different than being made of any metal. Plus with electric pickups it doesn't really matter what it's made of
He said a "shiny fiddle made of gold." Kind of implies the whole thing is gold, but it's open to interpretation.
A humility competition.
I'm not the most humble person in the world, far from it. But I think I can (probably) at least beat the Devil in that. I mean, the dude thought he was better than God. He is, literally canonically, the most prideful being in existence.
Idk if that qualifies as a contest of skill though. Sounds pretty much like a "not being the devil competition"
damn, if I get to choose.. then it is not a fair game.
first, if he is there threating me to go to hell, then it is safe to assume that heaven is real.
challenge him to do something against his nature.
Challenge him to be the better kindest person, can't be a kind person if he sends people to hell.
Challenge him to enter heaven by merit.
The devil doesn’t send people to Hell. God does. The devil is just there to receive and punish the people God determined weren’t good enough for Heaven.
"He's sending us to eternal damnation because he loves us!"
-Christians who are in an abusive relationship with their god.
Hell, I don't even think canonically he has any kind of official position. The Devil isn't Hades. Hades has an official position - he's Lord of the Underworld. He's just as much a deity as any of the other Greek pantheon.
But the Devil? I imagine Hell as just a giant hole in the ground where God throws things he doesn't like. As the oldest and most powerful being in Hell, the Devil ends up running the place by default, but it's not a position of divinely-granted authority. He's just as much a prisoner there as anyone else. The jail just has no guards, so the prisoners end up running things.
They must have a lot of faith in their handjob ability if they think anything better would be worth selling their soul for.
I was just thinking the same, he doesn't have to put 100% of his effort in. Just 1% more than yours.
Devil is a busy angel with a lot of important work to do for god, who being omnipotent, clearly had a good reason to create such a being. I wouldn't want to waste their time.
I would opt for a contest of billionaire slaying with points awarded by the net worth of each billionaire.
Speed wanking, who could shoot first
I'd win every time
Whoever dies first wins. At least he wouldn't get your soul!
Whoever dies for the last time first
Why does this post feel like someone applied the Facebook CSS to the 4chan HTML?
I think I'd beat him in "self-loathing". /s
Considering that Lucifer was basically a narcissist, that tracks.