Playing Dark Souls is a unique, breathtaking experience. Famous for being ridiculously hard to beat, the game, released by FromSoftware in 2011—and remastered in 2018—was a lot more than just challenging. It expanded on a new kind of gameplay created by its predecessor, Demon Souls, which punished the player for dying. Every death meant that all the other enemies fought previously would be revived, as well.
There was no other way around it: the player needed to improve their skills by—as much of the community would put it—"getting gud." If anyone dares to stand up to the game's horrors, increasingly tough bosses will eventually pose another challenge. All of those bosses are unparalleled and memorable—not especially unlike a great date, however absurd the comparison might be.
Bell Gargoyles
At the Firelink Shrine, the first main location of the game, the Crestfallen Warrior mentions that the Chosen Undead shall ring the Bells of Awakening, and that’s really the only piece of direction in the early game.
The player finally reaches the first Bell of Awakening on the top of a church. On the roof, two inanimate stone creatures start to move, and the first double boss battle of Dark Souls begins. They might not be human, but they surely have the cool, aggressive look that many look for when swiping left or right.
Pinwheel
The Catacombs are a really, really hard area. A dense dungeon of juxtaposing tombs and mausoleums, there are a lot of Necromancers who keep resurrecting the skeletons all over, and there are a lot of skeletons, all viciously pursuing the Chosen One.
After a lot of unfriendly encounters with the undead, the player finally is faced by a three-faced figure in front of a bunch of books. Four blows with any weapon, and he’s out. He’s a reader, not a fighter. For anyone looking for the nerdy kind of guy, this is a match.
Four Kings
Remember the Nazgul from The Lord of The Rings? The Four Kings are not too different from them. They are the former rulers of New Londo, corrupted by darkness after being given fragments of a Lord Soul by Lord Gwyn himself. After turning all their knights into Darkwraiths, they fell into the Abyss—in other words, absolute darkness. They do have a bit of tragic gothic charm, though, if that's your thing.
Iron Golem
Sen’s Fortress is the most treacherous place in the whole game where simply everything is trying to kill the player, from arrow traps to giant swinging blades, reptilian guards all over, and rolling stone balls à la Indiana Jones.
At the top of the fortress, there is a really tough-looking giant humanoid figure, the Iron Golem. Although fighting him is not actually that hard, he is still a strong candidate for the buffest guy in Lordran.
Gravelord Nito
Powerful and edgy-looking: Nito, the lord of Death, is also one of the holders of a Lord Soul. As if his rule over the dead was not enough, Nito also has what is probably the coolest look of the whole series. Anyone who is into the goth look will definitely fall for his brutal skeleton body made of skeleton bodies.
Chaos Witch Quelaag
Although she is a half-naked woman, she is also a half-flaming monstrous spider thing. Quelaag is a fitting boss for Blighttown, the buggiest area of Dark Souls.
To beat Queelag, the Chosen Undead needs to go through a hard battle, and that is the only way to reach the second Bell of Awakening. Whoever is not easily scared by sets of eight hairy legs will find in Queelag a powerful, fiery companion.
Gwyn, Lord of Cinder
If you want power, this is it; Gwyn, the final boss, is at the top of the food chain in Lordran. He is the dream of anyone in search of a sugar daddy. It is too bad, however, that the final boss fight might be a little disappointing. Gwyn is not as fierce as he may seem, but give him a break: he’s been around for too long, and the game still revolves around finally beating him. He’s the real deal.
Dark Sun Gwyndolin
Gwyndolin, child of Gwyn, is not a mandatory boss. Gwyn is a very androgynous character, being a brother by Gwynevere despite a very feminine figure. Fighting this mystical being is an option for those willing to dive deeper into the story. It turns out that Gwyn started the Dark Moon covenant and is the one behind the illusion of Anor Londo still being at its height. A magical date by the moonlight? Gwyndolin is the way to go!
Knight Artorias, The Abysswalker
One of the original four knights of Gwyn, Artorias is a sad figure. Once the greatest swordsman of all, he discovered the ability to walk the Abyss of New Londo. When Princess Dusk of Oolacile was captured, he traveled to the Abyss, only to be defeated by Manus. Before being corrupted by the darkness, though, he used his shield to save his pet, the wolf Sif. He would probably swipe right on any “must love dogs” dating profile.
Crossbreed Priscilla
A very tall woman with a scythe, a tail, and invisibility, Priscilla is actually half-dragon. She is an optional boss from the Painted World of Ariamis, a whole world that exists behind a painting in Anor Londo.
She is a little more optional than the other optional bosses, though: if the player chooses to simply walk by her, she will not attack. The most dateable of all Dark Souls bosses, in the end, is the most peaceful one.