୨୧ Hellbound ୨୧ Hazbin Hotel & Helluva Boss Fics

Best To Worst Lovers ୨୧Overlords୨୧

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I'm pretty sure Sir Pentious is more of a crimelord (what's the difference?) but I included him anyways. And Stolas is a prince but whatever.
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Lucifer
He might be the King of Hell, but he sure knows how to treat his partner. If you're romantically involved with Lucifer then be prepared to get only the best that the 9 Circles have to offer.

Benefits of Dating:  The entire relationship is a benefit.
Drawbacks:  He has a habit of micromanaging your social life (doesn't like you hanging out with certain demons).

Alastor
What you see is what you get with Alastor. Both in the streets and behind closed doors, The Radio Demon is a gentleman if nothing else. Despite this, you'll never be able to shake off the looming threat of his murderous habits- even if he promises you're not in danger.

Benefits of Dating:  Getting to eat his mother's jambalaya at least once a week.
Drawbacks:  The permanent speeding your heart does when he's nearby (is it love or fear?)

Stolas
Since Stolas is a married man, he'll already be a pro at working out a flexible schedule... for himself. If you're busy but he's not, then expect to receive a lot of calls and text messages. Aside from that, Stolas is a very compassionate lover and will listen to all of your problems if you ask him to.

Benefits of Dating:  He makes sure you take care of yourself.
Drawbacks:  Doesn't take a hint very well...

Sir Pentious
He's not a very good lover, but that's only because the standard relationship is different than what it was during his time period. He tries his best to be romantic, but sometimes he can't help acting 'old school'. These methods (while appreciated) don't catch on with you very well. You'll probably have to explain some things to him if you want the relationship to progress into something you're both comfortable with.

Benefits of Dating:  He treats you like a Queen.
Drawbacks:  The likely difference in time periods can lead to confusion/frustration on both ends.

Vox
Vox is not a gentleman by nature- though sophisticated (to some extent) he cares for few demons that aren't himself. Luckily you're one of them, so in the relationship he pulls out all the stops. However, he has this habit of pushing you aside in favor of his overlord friends. If they were out of the picture, then you'd surely have all of his attention (but don't go yandere, it won't end well for you).

Benefits of Dating:  You get premium cable.
Drawbacks:  His jerky attitude is so subtle that you'll never be able to call him out on it.

Valentino
No hate to the Valentino stans, but he's (currently) the worst character in canon to love. Maybe it's different if he actually cares about you and not the boost you give to his reputation. But I feel like even then he'd do some insensitive stuff.

Benefits of Dating:  He gives you whatever you want.
Drawbacks:  You have to give him whatever he wants.

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I tried to make the things I wrote as accurate as possible. Of course when we get more screentime of characters like Vox and Lucifer I'll probably have to publish a rewrite of this chapter.

What order would you put the overlords in? I'd actually put Sir Pentious and Vox if we're talking headcanons.

~𝕚𝕘𝕟𝕠𝕣𝕒𝕞𝕦𝕤𝟚𝟘𝟚𝟘

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