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Stotter
Wallet After Summer Sale -

(Laying in bed, literally not minding her.)  
Chrysalis: As thanks for allowing me to use this hiding space, I grant you permission to give love to me of your own free will. I do warn you that you’ll feel quite drained afterwards, but after your first time, you might want to give me more and more until I’m satisfied.  
(…)  
What? You act like I said something strange.
Evowizard25

@dynamicv  
Well with the comet, she knew very well what it would do with Twilight’s magic. She knew it would make Twilight very powerful, which is why she wanted to drain her. Chrysalis just wanted to gloat to Twilight, BEFORE restraining her and the comet arriving. That and in her episode, just letting them get out of their restraining goo and turning a back to them because she thought she won.
 
Chrysalis’ weakness is overconfidence and the habit of never learning from a defeat. She repeats her mistakes because she’s too full of herself to realize she made one.
dynamicv

@Background Pony #A46E  
@Evowizard25
 
Personally, here is what I think the reason is for Chrysalis’ failures: she lacks proper knowledge of pony magic. The fact that she asks Twilight for magic lessons indicates that she lacks the kind of magical knowledge that makes Twilight so powerful. It’s what leads her to being defeated.
 
The specific events that make her lose:  
-Cadance restoring Shining Armor, which she initially dismisses as “a ridiculous sentiment”.  
-Twilight Sparkle using the comet’s magic surge against her: she didn’t know how strong Twilight was.  
-Celestia defeating her at Trot: she didn’t know how strong Celestia was back then (This also could explain why she was surprised to beat Celestia in ACW: she already had a run in with her).
Evowizard25

@Background Pony #A46E  
She started gloating over them, kept her back to them, had no guards looking at them and didn’t think for a moment that them getting out of their bindings would do anything.
 
That and in the comics, before she could drain Twilight after bargaining her friends’ lives, she told her that she was going to kill her friends anyways……She did this right before a comet amplified Twilight’s powers tenfold.
 
Chrysalis has a bloated ego and no matter how many times she fails, she never once learns from it because she blames everyone else for her failures. {Which she could have easily avoided had she not been so cocky.}
 
Don’t get me wrong. She’s still enjoyable, she’s just no master mind.
Background Pony #AE80
@Evowizard25  
Well, when you think about it, she only lost because of a series of random events that she couldn’t possibly have foreseen. Granted, it was all because she made the mistake of putting Twilight and Cadence in the same place, but still…
Evowizard25

@Mr. Horrible  
Errr….Chrysalis isn’t all that ‘smart’. She’s too full of herself and her plans are, honestly, made up on the spot it seems. She has an ‘endgame’ but everything else is just thrown about as she goes along.
 
I always see Chrysalis as a wannabee villain. You know, the ones that try and ‘rule the world’ and do something evil, but they blunder epically and kind of suck at being evil.
Background Pony #14DC
It’s dusty and very cramped under there. I haven’t clean under there in years, so good luck.
Background Pony #AE80
Bring it on. I sleep with a jumbo-sized can of Raid®. Let’s see who will win…
fixman88
Sapphire - For users who have donated to the site
Happy Derpy! -
Bronze Supporter -
The End wasn't The End - Found a new home after the great exodus of 2012

Poni since '84
Chryssy, if you’re gonna hide from somebody you might not want to tell them…  
Besides, my bed is out of the question since I have a loft bed (‘under’ my bed is where my computer desk and chair are).
Magic Man

@Mr. Horrible  
@Mr. Horrible
 
Well, one must keep in mind that that is what Chrysalis was always meant to be, though Katie and Andy were the ones to give her more of a sense of humor. It’s really only the fanboys who’ve built up this false image of her as this wimpy crybaby who the ponies oppress and who just needs a hug. And no matter how truly black-heartedly evil they make Chrysalis, her fanboys will always make up whatever excuses they can muster.