An interesting thought to ponder.

And attempting to answer every aspect of your post would take me, personally, loads of research into other aspects of history in which I am less informed.  So, I'm going to stick with the purely Tudor stuff:

I certainly think that if Mary had been born a male instead of a female–and had survived (that was the catch…I mean, H8 and KoA had bore male children, but none of them had survived more than a couple of months) then H8 would never have even entertained the notion of leaving KoA.  That doesn't necessarily mean that he wouldn't have continued having mistresses, but AB was pretty staunchly opposed to becoming just “another” mistress, so I don't think that Anne would have even factored into the picture.

Of course, you can also look at it from this point of view:  Maybe H8's boredom with KoA had very little to do with Mary's gender.  While it certainly played a part later on in the Great Matter and became one of Henry's main points used in proving that their union was invalid, it may not have factored so much in his initial decision to leave KoA.  He may have truly been a man plagued by his passion for AB.  Let's be honest, he really wanted Anne for nothing more than a mistress until she refused–after that, things sort of got out of hand.  He may have been so blinded by lust that he might have still left KoA despite male-Mary's sex.  I don't think he ever would have declared a male heir born to KoA illegitimate, but it may not have changed the course of immediate history.  Long-term, perhaps, but not immediately.  

Hi Mark and welcome. Oh, I'm glad to hear that because pondering WWI, WWII, and France not being France was giving me a headache.

Henry would have been so proud.  Katherine would still have to ignore Henry's mistresses.    Anne was not, nor would she ever become mistress material.  Mary would still become a mistress.  So would Elizabeth Blount.  Richmond, however, would not have been raised so high.  I think there would have been a very long line of mistresses.  (Longer than there is already.)

 However, I believe that Anne and Henry were fated to be together.  I think Henry would have moved heaven and earth to have her.  It would have meant marriage no matter how I look at it.  I think Henry and Anne would usher in religious reform. I can't picture a 'what if' scenario without these two being together.  Hopefully, if and when Henry sets Katherine aside, he would keep in mind that she gave him his son and not be cruel to her.  I don't see much difference other than Mary being a boy and remaining legitimate. Of course, Henry would treat him with more respect than he did Mary. 

I like to think that Henry and Anne still would've ended up together even if Mary had been born male.  I think Henry would have stayed married to Katherine but taken mistresses, perhaps even Anne even if she was married to someone else.  And when Katherine died naturally in 1536 I like to think he would've then married Anne (providing she was a widow at that point!)  I just think they were two people who were destined to be together even if it was for a short time.  Of course Elizabeth would never have been born, Mary (as a boy) would've become king and the history of not just England but the world would have been rather different….

I think Henry’s love of Anne and his ambition would ha come regardless of Mary having been a male. Though it is questionable that he would have dared dethrone the mother of the heir…

I don’t think Anne would have become Henry’s mistress. She was pretty adamant about that, even before marriage to Henry was on the table. It’s easy to overlook the fact she was actually very religious and it was against her beliefs, as well as having the example of her sister before her – used till Henry got bored, then cast aside with nothing but a ruined reputation. I think Henry would have pursued her for some time, but eventually he would have moved on (doubtless with very bad grace!)

If Mary had been a boy, I don’t thnk Henry would have divorced Katherine. She would still have refused to comply, and Henry couldn’t be rid of her without their child being made illegitimate. She would probably have died in the early 1530s though just the same (although Henry’s appalling treatment no doubt speeded up her end) and Henry would have remarried. I think if he was still hankering after Anne he might have married her then if she was still single (would Henry have vetoed any marriage plans do you think? Out of pique or jealousy?) Anne wouldn’t have been the hated “other woman” then either. Without the desperate need for a male heir, maybe she would have remained married to him…

MarkM said

Been pondering some alternative histories. Mainly, what if Mary had been born a male. Thinking not just the ramifications for Tudor life, but for our own time as well. Would our world look different different?

I don’t know how I managed to miss the OP….I don’tthink the world would look too much different today.

What if England never split from Rome?

THere would still have been the Reformation though it would have been on a smaller scale since the presence of an almost totally Protestant state in England was a promise held out to the more moderate Protestants of Europe. Other countries, principalities and dukedoms would still have sceeded from the Vatican though.

What if Spain and England remained united?

Only until KAtherine’s death, though even before that Henry was capable of not wanting to be a jumior partner in that allience and he had never forgiven Ferdinand for making a seperate peace with the French king. Charles V wasn’t a big fan of Henry either.

Would France exist today or would the joint English and Spanish armies have wiped them out?

France would exist since it was in the intereast of Henry to keep France and Spain separate in the same way I can’t see Charles wanting Henry to share part of France with him. A 3 way tie amongst Europe’s most powerful nations was useful to not only all 3 kings but lesser powers like the Germanic and Italian dukes, the Scottish kings, the Pope in both his secular and religious roles.

Would Germany and Itally have remained unchanged?

Since both countries were formed from at first loose political amalagams and gradually unifed under a dominant ruler, they would still have become the countries they are today. Possibly faster, possibly slower…

If no, would there have been a WW1 or WW2?

Yes, the decay of the Habsbug Empire nad the rifts exposed as well as the various treaties holding Europe stable would have eventually made a war there inevitable. Though would England have had an Empire to call out such large numbers of troops? And would events like the annexation of German South West Africa( now Namibia) have taken place.

If no French support, would the US have been able to split from England?

Probably..since there was assisstance from the Netherlands and Spain as well as France..However, had the Napoleonic Wars then not taken place, England( or would it be Great Britain by then, would there have been the joint crowns of Englan and Scotland?)* would may had plenty of troops for when the fledging USA tried to invade Canada in 1812….USA may have been retaken …

Would the Pilgram’s have ever even bothered to sail there? Would Latin America had more of an influence from England rather then just Spain?

Almost certainly, the Pilgrims would have gone as would anyone else who had the money to make the journey. LAtin America probably still would ahve been divided between Spain and Portugal with those few pesky English and French counties in the north of Latin America and in Central America.

* Would England and Scotlan be one or two countries? An adult king of England could possibly have be seen as a better suitor for the young Mary of Scotland than an underaged French Dauphin. ..Could England have totally conquered Scotland and not neeeded a Scottish bride?

Mary’s greatest tragedy was that due to Henry, she was both too valuble and too valueless to marry when she was of an age to have healthy children.

That was where Mary was a valuble bride. The last thing Henry needed in England was a too big for his boots English noble trying to use Mary to gain extra power and influence over Henry( not that it would have happened!)..

Any English, Welsh or Irish noble interested in marrying Mary instantly was suspect. However I can’t see Henry palming off his daughter on some no-body from Nowheresville either.

Henry Fitzroy had marrried the daughter of the Duke of Norfolk. I doubt if Henry would have let Mary marry below that kind of noble station given the fact she was of royal blood on both sides.