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I had asked this question a few weeks ago but got little response so I thought I'd try again.

Anne Marie Louise Duchesse de Montpensier, also known as le Grand Mademoiselle, was the greatest heiress of her time, inheriting 5 duchies, the Dauphinate of Auvergne, and the Principality of Dombes from her mother. So she would have been a great catch for any European Monarch. Charles II, on the other hand, was less of one. Exiled, pennyless and powerless, Charles was a sad figure for almost 16 years, until his unexpected Restoration in 1660. Back on topic. Several times a match was considered between the two. The first was between 1646-1648, when Charles had fled into exile and lived with his mother. The second, in around 1651, was shortly after Charles escaped France. And the third, around 1660-1661, was after the Restoration. So what if the match had happened? Would Charles and Anne have issue? Would the Stuarts be allowed to hold on to some of le Grand Mademoiselle's lands? Would this help or hurt England in the long run?

A few things to think about before anyone comments. 1. If they marry during one of the first two times the match was brought up, I doubt that the French Court would expel Charles from France, as he would be a French noble and member of the Royal House of France by marriage. Nor would the Royalists be completely broke during their exile. 2. Le Grand Mademoiselle's marriage could have repercussions for her actions during the Fronde, a French Civil war between Cardinal Mazarin and the leading French Nobles, led by le Grand Condé. OTL she took control of the Bastille and fired on the Royal Army, which ended up costing her any chance of marriage. So this event would probably not happen ATL, with Anne being titular Queen of England, Scotland and Ireland by this point, and would have more to lose, both for herself and her husband. 3. With no marriage to Catherine of Braganza, England wouldn't acquire Bombay, thus potentially negating England's, and later Britain's, Indian Empire. Though one of Charles's brothers could potentially marry Catherine, thus still bringing Bombay to England. And finally 4. The House of Stuart would be financially independent from Parliament, threw their French holdings. Even if Mademoiselle has to give up some of her lands (which is very likely) she'll still no doubt retain some of them.
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