You’re going to regret a lot of things in this life of yours, but you’re never going to regret things quite like Voldemort probably regrets things. I mean is there anything more embarrassing than being hit with your own deflected Killing Curse and unintentionally creating your own mortal enemy out of a BABY? Unlikely. Looking back, we’re betting he had one big regret (see above), but that’s not to say he didn’t also have a bunch of little ones along the way:
#10: Spending time with Wormtail.
I think we can all agree that, Umbridge notwithstanding, Wormtail is just the worst of all possible people. I would rather eat mayonnaise forever than have to hang out with him for any length of time. I would rather lick a gas station toilet seat than tether my well-being to his traitorous carcass. Even if he hadn’t sentenced the Potters to death, I would only hate him slightly less. I don’t even know what we would talk about. He’s just kind of the human equivalent of stepping in dog poop. You know?
#9: Leaving a fully functional Portkey just sitting there.
Good thing Harry had a convenient escape route in that graveyard. Why did no one take care of this? Who was in charge of this? Was it Adolphus? He was in Azkaban. No wonder. This is just what happens when you delegate.
#8: Trusting Lucius Malfoy with a piece of his soul.
Lucius Malfoy is not a reliable man. He flung Voldemort’s precious soul-diary at his rival’s offspring the first chance he got, and he never looked back.
#7: Trusting Bellatrix Lestrange with a different piece of his soul.
Given that the only thing standing between them and a Horcrux was a dragon, a few drops of Polyjuice Potion, and some minor fraud, I’m just surprised Harry & Co. didn’t storm the bank earlier. This was rudimentary stuff, Bells. This was amateur hour.
#6: Choosing QUIRRELL of all people to attach his face to.
Now, it’s not Voldemort’s fault that Quirrell was the first impressionable idiot to come bumbling his way through some far-flung Albanian forest. Dude was simply working with the options available to him. But oh, boy. He had to listen to Quirrell snore for a year. I bet it was real sweaty under the turban, too. Voldemort did not ask for this. He asked for a human vessel to help him rise to power. How hard is that?
#5: Not killing Harry on any one of at least nineteen different occasions.
How many times did Harry slip through Voldemort’s creepy fingers? The answer is too many. Given the opportunity and maybe a weapon, like a musket or a sword or something, I think even I could have killed Harry by at least book three.
#4: Making his Horcruxes incredibly symbolic and meaningful.
Who could have foreseen that concealing his soul in several mildly well-guarded artifacts all over Great Britain (instead of, you know, several grains of sands in the depths of the deepest ocean) could have possibly gone awry? I guess hindsight is 20/20.
#3: Not just setting the Potter household on fire.
That way he wouldn’t have had to interact with anyone who could potentially sacrifice themselves and leave behind a love shield that would create a whole slew of problems a few years down the line.
#2: Sending a teenager to murder his ideological enemy.
This isn’t just because Malfoy couldn’t cinch the deal. It’s also because he managed to disarm Dumbledore using the only spell any of them had ever learned in six years of magical education, thus setting into motion a chain of events that would later equip Harry with the Elder Wand.
#1: Waiting for the end of the school year to kill Harry, thus granting him another solid year of magical education with which to thwart him.
This is an offshoot of a previous regret, but seriously. I’m starting to think Voldemort was afraid of success.