Grell Sutcliff - Character

Grell, as Madame Red's butler, is shy, awkward and fairly ineffective at his job, ruining even simple things like tea and getting lost when driving a carriage. In the anime, this results in his staying at the Phantomhive manor to be trained by Sebastian, but his presence only serves to annoy and anger the entire Phantomhive household. Furthermore, whenever he messes something up, he has a tendency to overreact and attempts to commit suicide in a fit of melodramatic humiliation. During one of these attempts, Sebastian stops this and it is at this point that Grell's pre-existing admiration for him becomes a full-blown crush (which turns out to be infatuation). Despite these constant attempts to end his life when he does something wrong, others only stop him to avoid the resulting large, bloody mess (Sebastian informs him that he can kill himself off the Phantomhive premises, indicating a lack of friendship between himself and other servants). He eventually does this so often that even the Phantomhive servants give up on trying to stop him, much to his surprise.
As a Shinigami, however, he is over-the-top and flamboyant, with a tendency to use female nouns and pronouns when referring to himself (called onee kotoba, "big sister speech", this is a common affectation of gay and MTF transgendered people in Japan). Grell refers to himself with female terms many times in both the anime and manga, and in the manga and character guide (written by the author) has expressed a desire to have a female body and the ability to have a baby. In the musical, he explicitly asks to be referred to as 'she', not 'he'. He also has a tendency to put things in terms of theater, referring to Angelina's death as the falling of curtains on a theater act, and comparing his relationship with Sebastian to the famous play, Romeo and Juliet. He apparently has feelings for Sebastian, much to the latter's disgust, and gives Sebastian an affectionate nickname (varies depending on translation: Sebas-chan in Japanese, translated by some fansubs as "Sebby", by Yen press as "Sebastian-darling" and by Funimation as "Bassy"). Despite his overwhelming love for Sebastian, he seems well aware that Sebastian despises him; in episode 10 of Kuroshitsuji II, the two have a "tea date", but Grell is very frightened throughout the meeting and keeps mentioning that although it's what he has always wanted, it doesn't feel right.
Although (in the anime, not the manga) Grell realizes that Sebastian does not return his affections and even finds them distasteful, he is so smitten that he allows the Demon to take repeated advantage of him, willingly trading his assistance for small favors (such as Sebastian striking handsome poses for his camera) even when that assistance results in injury or embarrassment. Apparently, he feels that any attention from Sebastian is better than none at all. (In the manga Grell is far more serious, capable, & competent, and simultaniously tries to kill Sebastian while flirting with him).
However, his affections are not limited to Sebastian, as he seems to find men, in general, attractive. For example, with William Spears, while he calls him a sadist, he seems enamored by his eyes, saying they send chills up his spine. In the anime, after seeing Undertaker's eyes, he immediately says: "Hold me" (Also a double-entendre in Japanese for a sexual proposal), indicating he finds him attractive. He also hunts down Pluto, saying he made his "hunk radar" go off. In particular, he seems to favor those he deems immoral.
Initially, it would appear that the other Shinigami do not seem to be overly fond of him as William constantly refers to him as "trash". However, both the manga and musicals imply that only William has a problem with him, as the other Shinigami respectfully call Grell "Sempai". Ronald Knox in particular is exceptionally fond of him, as Ronald always refers to him as "Senpai" and takes his advice on things over William's.
Grell's favorite color is red. He is described as the Shinigami in red by Angelina, commits the Jack the Ripper murders so he can paint "ugly" women red with their blood, and says ordinary women are not fit to wear the color. He tells Angelina that he will join forces with her because of his empathy with her desire for a child; he too wishes to be able to give birth, he says, but is unable to because he's a man.
Grell has two distinct personalities. Most of the time in the anime he is cheerful, if somewhat sadistic, with a playful flirtatious quality, and is usually seen whining about William or flirting with Sebastian. Apparently he is apathetic to the fact that neither one has any interest in him, as shown in the third OVA when William stabbed him in the head twice, Grell didn't seem to care that there was blood running down his face, rather, he simply continued to flirt with both William and Sebastian. However in the manga, Grell is typically bloodthirsty & will do anything for the desired results. When Undertaker causes a cut on his face in the manga, he said he could never forgive someone for hurting his face.