Prince Charming never heals Shadow Yukiko more than once, so its nothing more than a really, REALLY lame scare tactic by the developers to try and snake your attention towards him so Shadow Yukiko can tear you a new poophole.
Just use Mabufu with Chie, and you'll knock him down for a few turns. Once he's up, Shadow Yukiko casts that spell(I think it is Ice wall) that makes him immune to his only major weakness. But by the time he's gotten back up and she's been able to do that you should have her down to the point where he won't be much of a factor in the battle.
What REALLY helps is to get a Valkyrie, of the Titan Arcana, and get it to at least level 10, at which it gets Media, which makes the battle A LOT easier. Also, theres another persona which has a name I can't remember that has Red Wall, which you can cast on Chie for when Shadow Yukiko starts using Burn to Ashes.
None of the boss fights in the game are very hard, IF you level properly and get good weapons, armor, and accessories from Daidara's Workshop, or golden chests(And also, defeat every single bonus boss for each dungeon to get mad good gear for your first playthrough).
She's one of the hardest bosses considering how early in the game she fights you, after Shadow Yukiko, you won't have much trouble with any of the bosses so long as you use appropriate strategies, at least not until the final boss which I will leave anonymous for the story's sake(I'm referring to the true ending final boss here)...
That one is a huge butthole...
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