December 1516-August 1517
December 1516: Queen Catherine miscarries. She sinks into depression, especially as Henry once again falls into the arms of a young lady of the court.

January 1517: Elizabeth of England officially arrives at the French court. She is praised for her beauty and precocious elegance. Margaret, Countess of Alencon and Regent of France gives birth to a daughter, Louise. While she is still weak, Francis, Count of Angouleme steals the regency and captures Margaret, her husband, and children. They imprisoned in fine rooms at a countryside chateau.

March 1517: Despite his young age, Ferdinand VI assumes the regency at 14. He is known to have grown rapidly (being fully able to preform sexually by his 13th birthday) and has now impregnated his bride, Queen Isabella of Portugal, who fortunately goes into labor prematurely. The baby, christened Ferdinand after his father, is frail due to his premature birth, but manages to cling on to life. To the surprise of doctors, Queen Isabella recovers.

April 1517: Eleanor, Princess of Portugal gives birth to a second son named Manuel after her ailing father-in-law. Manuel’s health is slowly failing. It was first thought to be depression over his wife’s death, but physicians are now unsure as to what is killing the Portuguese king.

May 1517: Seeing as his brother’s wife is pregnant and seems to be alright, Charles riskily decides to consummate his marriage to Anne of Hungary. While Isabella survived the birth, Anne was not so fortunate. The birth was far too difficult for her immature body, and she dies not 30 minutes after giving birth to a son named Philip. He is alive for the mean time, but much like his newborn cousin Ferdinand, is barely clinging to life.

June 1517: John, Duke of Rothesay is officially betrothed to Princess Margaret of England. The betrothal is sealed by a meeting of the two Royal courts at Scotland. The meeting goes mostly well, until the Kings of England and Scotland get into a drunken braw over a young Scottish maid whom they were both interested in spending the night with. In the morning the two men publicly agree to friendship, persuaded by their wives. While returning to Scotland, King James dies in his tent, allegedly from sexual over exhaustion after sleeping with the same maid whom he had fought over, whose name has unfortunately been lost to history, but more likely from a massive heat attack. Margaret of England, now Regent of Scotland, rushes to have her son crowned King John II of Scotland.

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James IV, King of Scotland

July 1517: Archduchess Mary of Austria marries King Louis II of Hungary. Isabella, Queen of Denmark gives birth to her first child, a son named John.

August 1517: Claude, Duchess of Savoy gives birth to a stillborn son.
 
September 1517: Marguerite is supposedly dead inside the chateau after it mysteriously burned down. Well, her body can't be found anyway. Her husband is definitely dead though. As are her children. The tiny burned corpses are the only reason she is free from suspicion. Surely nobody killed their own children so cruelly. Francis orders an investigation.

October 1517: widowed twice before reaching majority, Charles swears to remain celibate and even makes moves towards designating his brother as his heir. His regents do not appreciate that move.

November 1517: Manuel of Portugal dies in his sleep, being succeeded by his son, John. The prince of Wales, too, is sent off to Ludlow with Renee.
1. The whole mass killing goes against the rules, and it’s super unlikely and bizarre anyways.
2. I really don’t see Charles giving up on remarrying, it’s very out of character.
 
1. The whole mass killing goes against the rules, and it’s super unlikely and bizarre anyways.
2. I really don’t see Charles giving up on remarrying, it’s very out of character.
Supposedly dead. It was left ambiguous. It is entirely possible they are alive and escaped.
Also, Charles gave up on remarrying IOTL after he lost ONE wife. If he lost two in quick succession...
 
Supposedly dead. It was left ambiguous. It is entirely possible they are alive and escaped.
Also, Charles gave up on remarrying IOTL after he lost ONE wife. If he lost two in quick succession...
1. You very clearly stated that husband and kids are 100% dead. The entire affair is foolish anyways. If it’s a bizarre mass killing don’t put in the timeline. The rules are clear.
2. He’s practically a child here and needs an heir. Baby Philip is very sickly, if he is even still alive (you implied in the post that he died).
 
September-November 1517
September 1517: Marguerite is supposedly dead inside the chateau after it mysteriously burned down. A dead woman was certainly in the chateau, but its corpse was burned beyond recognition. Her husband and her children are alive, but Alencon swears that he has not seen her in weeks. Francis orders an investigation into the disappearance of his sister. Francis' mother, Louise of Savoy, falls ill.

October 1517: Widowed twice before reaching majority, Charles swears to remain celibate and even makes moves towards designating his brother as his heir. His son, Philip had succumbed to a chill, devastating Charles. His regents do not appreciate that move - he is young and still fertile. Another bride is sought for him - but with two wives dying shortly after marriage, he is beginning to be seen as cursed. No replacement is immediately found, and Charles secretly hopes none is ever found. Surely his brother can sire enough heirs to secure the dynasty.

November 1517: Manuel of Portugal dies in his sleep, being succeeded by his son, John. The prince of Wales, too, is sent off to Ludlow with Renee. Paranoid, as Henry VIII remembers what happened to his brother, he personally goes alongside his son, leaving his wife as regent. Katherine takes to this with enthusiasm.
 
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Margaret, Countess of Alencon and Regent of France gives birth to a daughter, Louise. While she is still weak, Francis, Count of Angouleme steals the regency and captures Margaret, her husband, and children. They imprisoned in fine rooms at a countryside chateau.
…Francis would never do this to his beloved sister.
 
…Francis would never do this to his beloved sister.
Yes, they were very close in OTL, but Francis was misusing the regency, so Margaret snatched it for the sake of the little King (who had been neglected under Francis). From that point on, the two were enemies.
 
December 1517-June 1518
December 1517: Catherine of Aragon, Queen of England, is pregnant again. The King celebrates, hopefully this time a healthy baby is born. Juana, Duchess of Suffolk gives birth to a daughter named Margaret. In France, Regent Francis discoverers that his sister Margaret did not die in a fire, but was out riding her horse when the fire occurred. When she approached the castle, the horse became spooked, and Margaret was thrown from her horse, dying immediately. The nuns who had her buried at the nearby convent give testimony, and Margaret’s body is returned to Paris. On the way, Charles of Alencon dies, possibly of grief, leaving his son Charles as Duke of Alencon. Francis, truly saddened and guilty over his sister’s death, officially adopts her four children: Charles (b. 1513), Margaret (b. 1514) Louis (b. 1516), and Louise (b. 1517). This is a great joy to Francis, as Countess Anne has had trouble conceiving children.

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Margaret, Countess of Alencon

January 1518: To secure the kingdom, Regent Francis officially marries King Louis XIII to the now Queen Elizabeth of England. The marriage is, of course, not consummated, seeing as the two are only five years old. France, after constant inner-feuding, finally seems at peace with this marriage.

February 1518: Isabella of Portugal, Queen of Castile and Aragon, provides her husband with their first daughter, Infanta Isabella. The two are remarkably happy with each other and are compared to King Henry and Queen Catherine of England, who, despite Henry’s occasional infidelity, are referred to as ‘the Lover Monarchs’.

March 1518: King Ferdinand’s sister, Queen Eleanor of Portugal, gives birth to her own daughter, named Infanta Maria after her deceased mother-in-law.

April 1518: Charles V, Holy Roman Emperor carries out an affair with one Johanna Maria van der Gheynst. She conceives, and this pregnancy restores Charles’ desire to marry. The only problem is, exactly who should he marry? He eventually lands on Beatrice of Portugal, who, despite being a cousin, is passingly pretty, and comes from fertile stock. So he sends for Beatrice, even when he hears that Johanna Maria has miscarried.

May 1518: In Denmark, Queen Elisabeth gives birth to a daughter named Dorothea.

June 1518: Catherine of Aragon, Queen of England gives birth prematurely to a sickly daughter, who is christened Cecily. Despite her sickliness, the baby continues to live, and is treated by the best doctors in all of Europe.
 
July 1518 - June 1518
July 1518: After being churched, Henry sleeps with his wife again, trying to get another son. Well, it is not as though sleeping with Katherine is a chore for him - she is still beautiful, despite her aging; the streaks of grey in her hair and the stretch marks on her belly only show Henry that she has gone through great ordeals to become his perfect queen. She becomes pregnant again, much to their joy. Henry even allows Katherine to name this child anything she wishes, provided that it is able to be pronounced in English (he had named all of their children before).

August 1518: Henry VIII writes a response to Colloquies by Erasmus, which had been published several months ago. Entitled Formalities, it is seen as a sequel of sorts to Erasmus' work, though notably focuses a lot on the joys of fatherhood. And this is a topic he knows well: he and his mistress, Elizabeth Blount, are expecting another child. Katherine tries not to react to it, but her sister, the Duchess of Suffolk has a lot to say. She notably treats Elizabeth Blount with an icy regality - which is a great improvement from how she treats the mistresses of her second husband...at least there is no opprobrious language involved this time. Regardless, Formalities becomes very popular.
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Joanna, Duchess of Suffolk (right) and Elizabeth Blount (left) in the show "Henry VIII's First Decade", a show depicting his first ten years as king of England. The inaccurate looks of both women - Joanna was a redhead, while Elizabeth was blonde - infuriated many viewers when it was released.

September 1518: Anne, Countess of Angouleme, dies of a miscarriage. Now that Francis of Angouleme is a widower with one sickly son (well, if you didn't count his sister's children, which he didn't), he decides to remarry. The question is...to whom? He has an eye on his long-term mistress, Francoise de Foix, but she is not exactly suitable as a second wife if he's childless. Well, he is young, he can decide soon.

October 1518: After the death of Claude, Duchess of Savoy due to difficult childbirth that resulted in a sickly daughter, Charles III of Savoy is in need of a new bride. Unfortunately, the English princesses are all too young. Henry wonders how he can benefit from this anyway. In other news, Queen Eleanor of Portugal is pregnant again, as is Queen Isabella of Denmark.

November 1518: Beatrice of Portugal arrives, she marries Charles in a lavish ceremony. However, she was not as beautiful as her portrait made her look. Infuriated at the artist for this deception, Charles does not consummate the marriage, though he tells his new wife that it is because she is too young for childbirth. Well, he's not wrong on that regard anyway - she was even shorter than Anne of Bohemia and Hungary had been, and she told him that she had not yet gone through the woman's bleeding. Therefore, she was still infertile, and bedding her would be useless. He impregnates Johanna Maria van der Gheynst again.

December 1518:
Christmas this year is a disaster - Elizabeth Blount snubs the queen openly, while the king's latest mistress, 19-year-old renowned beauty, Mary Boleyn, announces a pregnancy. The queen is devastated by her husband's open acknowledgment of his mistresses and bastards, and the formerly loving marriage starts to show cracks. Also around this time, Charles Brandon, Duke of Suffolk falls ill.

January 1519: Joanna, Duchess of Suffolk requests permission to travel around the world, as she wishes to reunite with her children. Although Katherine does not want her to go, selfishly liking that she at least has some family with her in England and fearing any accidents abroad, Henry VIII accepts this request. However, Charles Brandon is not allowed to accompany his wife and must stay in court with him. Elizabeth Blount also prematurely gives birth to a boy: Henry Fitzroy. His father endows him with two earldoms of Rutland and March, while his sons with Katherine get the dukedoms of Richmond and Somerset. A furious Katherine leaves England, accompanying her sister Joanna, after receiving her husband's permission. She would like to meet her nieces and nephews anyway...and she hasn't seen Maria in so long. She leaves letters to her children and to her husband. Queen consort of Poland, Bona Sforza, gives birth to a daughter: Isabella. Henry wonders if one of his sons can be betrothed to the Polish girl.

February 1519:
Queen Katherine gives birth prematurely to twin sons after a long and difficult labor. Due to her fight with Henry, she decides to give her sons Spanish names: Juan, after her brother, and Alfonso after her uncle. Although the English court insists on calling them by English versions of their names, she does not relent and speaks only Spanish to her children, which she knows Henry does not understand. The team of doctors switches from caring for Cecily to caring for the two boys. They stubbornly cling to life, much to Katherine's relief.
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Queen Katherine of Aragon holding her youngest son, Ferdinand.
 
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July 1518: After being churched, Henry sleeps with his wife again, trying to get another son. Well, it is not as though sleeping with Katherine is a chore for him - she is still beautiful, despite her aging; the streaks of grey in her hair and the stretch marks on her belly only show Henry that she has gone through great ordeals to become his perfect queen. She becomes pregnant again, much to their joy. Henry even allows Katherine to name this child anything she wishes, provided that it is able to be pronounced in English (he had named all of their children before).

August 1518: Henry VIII writes a response to Colloquies by Erasmus, which had been published several months ago. Entitled Formalities, it is seen as a sequel of sorts to Erasmus' work, though notably focuses a lot on the joys of fatherhood. And this is a topic he knows well: he and his mistress, Elizabeth Blount, are expecting another child. Katherine tries not to react to it, but her sister, the Duchess of Suffolk has a lot to say. She notably treats Elizabeth Blount with an icy regality - which is a great improvement from how she treats the mistresses of her second husband...at least there is no opprobrious language involved this time. Regardless, Formalities becomes very popular.
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Joanna, Duchess of Suffolk (right) and Elizabeth Blount (left) in the show "Henry VIII's First Decade", a show depicting his first ten years as king of England. The inaccurate looks of both women - Joanna was a redhead, while Elizabeth was blonde - infuriated many viewers when it was released.

September 1518: Anne, Countess of Angouleme, dies of a miscarriage. Now that Francis of Angouleme is a childless widower (well, he was raising his sister's children, but he didn't have any issue from his loins), he decides to remarry. The question is...to whom? He has an eye on his long-term mistress, Francoise de Foix, but she is not exactly suitable as a second wife if he's childless. Well, he is young, he can decide soon.

October 1518: After the death of Joanna, Queen consort of Naples, Ferdinand II of Naples is in need of a new bride. Unfortunately, the English princesses are all too young. Henry wonders how he can benefit from this anyway. In other news, Queen Eleanor of Portugal is pregnant again, as is Queen Isabella of Denmark.

November 1518: Beatrice of Portugal arrives, she marries Charles in a lavish ceremony. However, she was not as beautiful as her portrait made her look. Infuriated at the artist for this deception, Charles does not consummate the marriage, though he tells his new wife that it is because she is too young for childbirth. Well, he's not wrong on that regard anyway - she was even shorter than Anne of Bohemia and Hungary had been, and she told him that she had not yet gone through the woman's bleeding. Therefore, she was still infertile, and bedding her would be useless. He impregnates Johanna Maria van der Gheynst again.

December 1518:
Queen Katherine gives birth prematurely to twin sons after a long and difficult labor. Due to her fight with Henry, she decides to give her sons Spanish names: Juan, after her brother, and Fernando after her father. Although the English court insists on calling them John and Ferdinand, she does not relent and speaks only Spanish to her children, which she knows Henry does not understand. The team of doctors switch from caring for Cecily to caring for the two boys. They stubbornly cling to life, much to Katherine's relief.

January 1519: Joanna, Duchess of Suffolk requests permission to travel around the world, as she wishes to reunite with her children. Although Katherine does not want her to go, selfishly liking that she at least has some family with her in England and fearing any accidents abroad, Henry VIII accepts this request. However, Charles Brandon is not allowed to accompany his wife and must stay in court with him. Elizabeth Blount also prematurely gives birth to a boy: Henry Fitzroy. His father endows him with two earldoms of Richmond and Somerset. A furious Katherine stealthily escapes England, accompanying her sister Joanna. She would like to meet her nieces and nephews anyway...and she hasn't seen Maria in so long. She leaves letters to her children and to her husband, stating that she would return after a year. Queen consort of Poland, Bona Sforza, gives birth to a daughter: Isabella. Henry wonders if one of his sons can be betrothed to the Polish girl.
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Queen Katherine of Aragon holding her youngest son, Ferdinand.
A few problems…
1. Francis of Angouelme and Anne of Navarre did have a child together, Francis (b. 1513)
2. Ferdinand II of Naples died in 1496, so he died before the POD.
3. You said yourself that the baby’s name would be translated to English: so the baby would be actually christened John, even if his mother called him Juan. And Henry is never naming a son of his Ferdinand. Catherine seems to have become quite angry at her father in his final years anyways (you know, abandoning her in England). It’s probably worse because she would have heard from Juana how badly he treated her. Maybe the baby could be called Alfonso? It’s still very Spanish, yet also has been used in England before, so it’s not quite so jarring.
4. Catherine isn’t leaving England. She refused to leave her husband even after he tried to annul their marriage, shame her, and ruin her reputation. Even if Joanna goes, Catherine isn’t.
Else than that, very interesting!

EDIT: Henry’s not giving Somerset and Richmond to a bastard. He only gave them to Fitzroy in OTL because he had no sons. Those titles go to the twins. If you want to give Fitzroy titles, the Earldoms Rutland and/or March work better. And the babies can’t be born in December. At the latest they are five months along in pregnancy. It’s very difficult for babies to survive outside the womb at that age now, much less in the 16th century.
 
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A few problems…
1. Francis of Angouelme and Anne of Navarre did have a child together, Francis (b. 1513)
2. Ferdinand II of Naples died in 1496, so he died before the POD.
3. You said yourself that the baby’s name would be translated to English: so the baby would be actually christened John, even if his mother called him Juan. And Henry is never naming a son of his Ferdinand. Catherine seems to have become quite angry at her father in his final years anyways (you know, abandoning her in England). It’s probably worse because she would have heard from Juana how badly he treated her. Maybe the baby could be called Alfonso? It’s still very Spanish, yet also has been used in England before, so it’s not quite so jarring.
4. Catherine isn’t leaving England. She refused to leave her husband even after he tried to annul their marriage, shame her, and ruin her reputation. Even if Joanna goes, Catherine isn’t.
Else than that, very interesting!

EDIT: Henry’s not giving Somerset and Richmond to a bastard. He only gave them to Fitzroy in OTL because he had no sons. Those titles go to the twins. If you want to give Fitzroy titles, the Earldoms Rutland and/or March work better. And the babies can’t be born in December. At the latest they are five months along in pregnancy. It’s very difficult for babies to survive outside the womb at that age now, much less in the 16th century.
I have edited it. I gave Somerset and Richmond to the bastard because I made it clear that Henry and Katherine were fighting and this was a way to serve as a metaphorical slap in the face, but I changed it to your suggestions. Also, I stated that Katherine named the child because Henry let her have full freedom to choose...and she chose Ferdinand as a way to piss him off. Katherine is leaving England to be with Joanna.
 
I have edited it. I gave Somerset and Richmond to the bastard because I made it clear that Henry and Katherine were fighting and this was a way to serve as a metaphorical slap in the face, but I changed it to your suggestions. Also, I stated that Katherine named the child because Henry let her have full freedom to choose...and she chose Ferdinand as a way to piss him off. Katherine is leaving England to be with Joanna.
So I guess Catherine leaves England before she gives birth?
 
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