What would be the procedure to get a ''surefire'' Iberian wedding ?

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ElGranCapitan

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Fastest, yet somewhat controllable would be:
Restart until France rivals you and Austria
Select France as a rival
Improve relations with Austria, he will flip friendly with +100 and mutual rival after a few months
Ally but don't marry (don't marry anyone at the start), wait for your queen to die, she is 10 years older than your king
After the queen is dead throw around some marriages to get a new, younger queen
Disinherit Enrique

Due to the steps above you will get an event that gives you a Habsburg heir who should always be 0 years old, unlike regular heirs who are somewhat random
The Wedding can fire if your ruler and Aragon's ruler are different gender or one of you has a regency
Regency is easier to get and far more consistant. Since the starting queen is in her 50s the chance of her dying are rather high, therefore you should get a younger queen before going into regency
You can also do it without the Habsburg event, but then there's the chance of the heir being older, resulting in a shorter or no regency
 

Kurvix

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He asked different thing if i am right.
To get union of Castile and Aragon - works same for all in fact.
One of the ways is to have female as ruler on one of 2 nations and teh other is to have Aragon ruler die without heir. As i noticed in fact with Cradle if Aragon ruler dies witthout heir there is no succession war as Wedding is triggered.
TBH at the beginning u can now easily get yourself few strong allies - preferably France and Portugal and declare war on Aragon. From some odd reason their heirs are almost always generals and tend to die easy in battles. This will trigger 90% of time female heir or no heir which means u can make peace now easy. Even if Ruler dies and heir is still living (and he is rather old at that point) u can go for victory conditions show of strength or humiliate as option. Due to low prestige/power projection points there is huge chance that Ruler will die without heir or get female heir. Wedding triggers so easy that way.
One of risky options is that your Ruler dies and ""omfg is that" Enrique becomes king -he is infertile or something liek it which means he is most likely to die without heir. So what happens is next - u will have 2 or 3 events where u will be offered heir with weak claim (found in forest or as result of mingling with nobility). This usually triggers female heir. Not always but most of time (like 80%) or u might trigger event for Isabel as heir. Those are your options.
If u fail to make union in first 20 yrs of game it gets seriously hard to get it later. And might not trigger untill u research lvl 10 administration tech. By that tiem Aragon is either getting huge power either losing Naples and some provinces. All due to stupid ai making them go into war against way op enemies. If u can make Aragon ally u can keep it of trouble.
 

Slynx

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you just need a queen. (queen-consort works too)
so go and get one. (I guess weddings rise the chance...hopefully there are someone who will agree to wed you :D )
and throw away\kill Enrique and the starting king. (and don't forget that iirc you need to be at peace with aragon for even to strike) (make them as generals)
 

WJLIII3

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These are all strong and effective strategies, but I feel I've gotta contribute that, in my numerous, even uncountable games as Aragon, and many more as Castille, I've always used as my strategy: "Just do whatever you want and the Wedding will fire pretty soon." And that strategy has never failed me that I can recall.
 

Badesumofu

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The game is set up to make this very likely, and it's generally more a case of a player having to interfere to prevent it (which always aim to do as France, usually by forcing a Union on one or the other of Castile and Aragon). But the strat near the top of the thread for getting into a Consort Regency is probably your best bet to speed things up. It also has the benefit of getting Habsburgs on your throne which is a good thing (at least from a purely game-mechanical point of view).

You might also consider not rushing the union and ally-feeding Aragon a bit first. When playing France I tend to, if I can help them survive the early game, ally-feed Provence up as much as I can before the inevitable PU. It's AE free land that will ultimately be yours. Potentially free cores too when you inherit them or just hit the Spain button in your case.