I'll argue that however many times you need to retry an obstacle in a game has no bearing on it's difficulty, and that what really makes a game, how we say 'hard', is how many different ways you try to overcome that obstacle. This question may arise itself to you while you give some of your spare time to The World Ends With You, a comic book styled hack-and-slasher evidently drawn to be in tune with some interpretation of eastern popular culture, although it's a bit sketchy as to which, since I've never seen a comic come out of Japan where the mid-to-late-teen protagonists aren't in school, but perhaps I'm just a bigot.
The game involves running around central Tokyo, reading peoples minds to look for monsters. When you encounter a monster, you can then use touchscreen gestures in order to kill it before it kills you. You obtain these gestures by collecting various maguffins that people just leave lying around for the monsters to grab. Now, since you can only have a limited number of attacks in any one skirmish, you should consider which ones are more ideal. Or at least you would if they weren't all the same. There is no reason to swap out attacks for other ones, since each attack gains experience as well as the protagonist, and you might as well level up a basic set of attacks since levelling up all the ones you find would just take forever.
So you just keep using the same attacks again and again, like a wheel within a wheel until you stop paying attention to anything beyond the fundamental mechanics, because the sedate art direction certainly won't distract you. You forget why you're even doing this. But wait, I hear. There's a fashion trend mechanic that gives you bonuses for using certain brands of attack? That mechanic is easily broken by just using the same set of attacks you've been using, completely throwing aside the point of it all. Perhaps it would be rewarding if you had to work this out, but the game straight-up tells you as part of a narrative segment.
So we return to the beginning argument, as to whether the game is hard or not. Quite frankly, there's no challenge at all, you're just following instructions, and any sense of reward is quickly dismissed by the notion that everyone else got past that obstacle the exact same way, by slashing up on the touchscreen a few times. Oh, and don't bother with controlling your partner, it just makes it impossible to focus on anything.
Focusing on anything is something the scriptwriter evidently tried to do, but didn't quite manage. The premise is that there's this big game that youths are being thrown into and that you'll die if you don't win. The eventually-revealed true nature of the game tries to be shocking, but there's no sense of mystery before hand to draw you in. Having said that, some of the early segments are quite well done, but it just feels like very little effort was put into this one, so why should you put the effort in?