WI; All of Henry VIIIs Kids Survive... But as Daughters

A son who will not be born in England…and thus a hard sell as a future heir. If Charles wants any chance of his and Elizabeth’s son on the throne, he needs to play nice with Henry, which means supporting his annulment.
Hm. I mean, sure. I wonder, though, if perhaps Charles can ship Elizabeth off to give birth in England
 
Why? Henry's not likely to need Cleves and Bavaria on his side ITTL
Bavaria is admittedly a little less likely, but I still think Cleves is pretty plausible. Keep in mind, William married an Austrian Archduchess IRL - so England's ties there wouldn't harm any potential match
Not only is he much younger, he's not likely to even succeed as king. Especially since you have her older sister marrying his uncle
His brother Louis has died at this point, making him defacto second son. Plus that uncle would die a few years after the marriage date IRL - whether or not he is longer lived ITTL, I didn't picture him succeeding regardless. This means, a generation down the line, a similar match is struck, and just given the age difference between Henry's youngest and oldest kids, there is a sister still of 'breeding age' unmarried
These two hated each other...
Yet both Henry and Elizabeth considered marrying either them or close family - even if they have sisters as wives, that doesn't mean they have to get along
Are you assuming they elope? Who would approve of this ever?
This is meant to be synonomous of Elizabeth's relationship with him IRL. A very questionable match morally, but even some of her close friends encouraged her to marry him
 
English brides will make Henry VIII be the grandfather of Europe.
I wonder if this will leave enough descendants to have a haplogroup marker traceable back to him present across Europeans and European-Americans. Obviously this is nowhere near what Genghis has, but still.
 
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