Minty would:

Bed Holden
Wed Will Avery because he's the most appropriate of the bunch
Behead Christopher because poor person

Sponsor edition!
Theodore Gallivan Mikail Karim Roberto Devine

  

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Holliday would...

Bed Mikhail as he's handsome and ~fancy (read: exotic read: ve racism)
Wed Theodore because on top of being handsome, he is age appropriate.
Behead Roberto because she's not out to steal another woman's man or kill them, but here we are.

UPCOMING DEBUTANTES
Seneca Lestrange Grace Greengrass Nicolette Fernsby

  

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— graphics by mj ❤ —

Freddie would...

Bed Nicolette because she's classically pretty and Freddie's a sucker for a pretty face.
Wed Grace because she's probably the best-suited for him out of the bunch.
Behead Seneca because she seems terrifying.

UNMARRIED FISKS
Julian Fisk Nemo Fisk Dorian Fisk

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   Roslyn Ross

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— set by mj <3 —

Bed Nemo because she thinks he's attractive
Wed Dorian because he took Divination
Behead Julian but only because he's the only one left sorry

Men who are not super young and could think of at the top of my head edition:
Balthazar Urquart Octavius d'Orsay Evander Darrow

  

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set by MJ

Edna would...

Bed Octavius because DAMN.
Wed Balt bc easy access to her favorite student :P
Behead Evander because he's already engaged and Edna don't play like that.

TIME TO PLAY HOMEWRECKER EDITION
February Umbridge Roslyn Ross Diana Abbott

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   Roslyn Ross

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— absolutely DIVINE set by MJ —

Mikail would...
Bed February, seems like the most possible fun in bed.
Wed Roslyn, because of the whole Jewishness passed through the mother thing.
Behead Diana, she's almost too perfect.

Can't Introduce Her to Mother Edition
Florence Fox Ester Montgomery Fenella Goshawk

  

Freddie would...

Bed Florence, because you'd think she'd be good at bedding by now.
Wed Fenella, because at least she's got some skills that could bring in money when they inevitably fall from grace because of the marriage.
Behead Ester, because he couldn't wed a woman whose nude picture were everywhere. That is evidently where he draws the line.

Malfoyyyys
Estelle Malfoy Angeline Malfoy Victoire Malfoy 

  

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— set by mj <3 —

Thaddeus:

Wed: Victoire Malfoy - certainly meets his definition of a near perfect society wifey!

Bed: Estelle Malfoy - not bad to look at, good family, honestly he could do some thing with that socially!

Behead: Angeline Malfoy - weakness is worse than sourness


Heads of houses - a nice weird one!
Meserimus Valenduris Basil Foxwood Havelock Nott

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   Victoire Malfoy

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Interested in Higher Education? Join The Flint Institute of Advanced Magic
~
Interested in the esoteric dark arts?  Join the Knights of Walpurgis

Lannister would...

Wed: Meserimus Valenduris - They'll probably each have their own unique stories to share with one another from over the years (Gotta remember, our dear Lannister is over 500 years old!)

Bed: Basil Foxwood - I mean, come on, look at him

Behead: Havelock Nott - Sorry Mr. Nott!

Head of Department Edition...
Murdock Greyback, Lionel Lupin, Edric Umbridge

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   Basil Foxwood

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Magic by Elaine

Wed: Edric Umbridge - he seems like a peach

Bed: Murdock Greyback - I bet he's good in bed, so it would be a worthwhile tumble

Behead: Lionel Lupin - He could fit in the other ones as well tbh

Crazy Rich Asians
@"Natsuko Mountbatton" Octavia Fawley Ida Chang

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   Ida Chang

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Gin made something stunning

Doing this in an AU where Seneca can marry women because for all we know she might one day bed one and realize she likes it and beheadings aren't gender-specific activities. xD

She would:
Wed: Ida because she's a pureblood and also smart.
Bed: Natsuko because while she's a half-blood, she's interesting.
Behead: Octavia because she's too meek.

"Soph scrolled randomly through the CD and let her cursor land on a name until she had 3 male characters edition":
Algernon Astorwood Cleon Broadmoor Jude Wright

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   Ida Chang