Simp Rupert

Simp Rupert is a Boss in Elden Ring.

Location
Rupert is found in Cu'um's Castle. Players must defeat this boss to proceed.

Description
Simp Rupert appears to be an ordinary larger-than-the-player knight boss, with the added feature of having a unique mechanic known as "Money Shot". Rupert is also unique as the player can defeat him with an item, rather than traditional combat.

Lore
Not much is known about Rupert, as he is a quiet, depressing character; only speaking when Gawr Gura is present.

When Gura is present, Rupert will tell her that he is "her number one fan" and regale the tale of how he became Cu'um's "special little sauce boy", a title that he holds in high regard. Telling Rupert his title sucks results in him immediately cooming and causing the arena to become covered in his coom, slowing down player movement, showing he really is just a simp.

Rupert is unique in the fact that the player can "defeat" him without killing him, as producing a Shrimp given by Gawr Gura will instantly pacify him, leaving him cradled in a puddle of coom murmuring "Why?... Why?... Why can I not be thine little pogchamp? It is all I desire..."

Plot
Simp Rupert was left behind by Cu'um in order to guard the later's porn stash. Rupert however, was deceived into thinking he was taking on a sacred duty, as his affection for his master clouds his perception of reality.

Strategy
While Rupert is at first non-hostile, all options the player can take will lead to the boss fight. It is wise to use this time beforehand to apply weapon and body buffs. It is recommended to bring a Lightning-flavored Vape as he has asthma.

At half health, Rupert will unleash a pubescent scream, and he will grow 2 inches taller. During this phase, he gains new, wilder attacks as he enters a new "frenzied" mode. However, should the player make enough space between them, they can use the Shrimp item, and instantly defeat him.

Drops

 * Sticky Gauntlets
 * Cu'um's stash

Videos
https://www.youtube.com/watch?v=bUfift7822g