"Darling", also spelt "Dahling", is a common term of affection noteworthy for its idiosyncratic misuse by Chris. "Dear" is also used by him for the same purposes, albeit less commonly. While the term, when used by an adult male for an adult female, almost always carries romantic associations, Chris says that he uses it purely in a platonic manner and cannot understand why the objects of his affection find it creepy. It is possible that because Chris sees himself as a woman, he thinks he can escape the gendered meaning of the word, ignoring that an actual lesbian saying it to another woman would be only modestly less creepy.
"Darling" first appeared during Chris's edit war against Encyclopedia Dramatica. On 19 January 2008, Chris blanked his page, displaying what he intended to be a letter written by then-president George W. Bush ordering Encyclopedia Dramatica to remove their message. Therein, he uses the term "dahling" twice, first to address ED, and again to refer to himself as a "dahling US citizen." 
|Dahlings, by order of of President George Bush Junior, there shall be no naughty, grotesque posts of this dahling US citizen.
Any new posts, or deletion of this official message shall be found punishable to the fullest extent of American Law.
From the Secreterial Desk of the White House,
The President, George Bush
Many years later, the term would be resurrected as Chris's default form of address for DoopieDoOver, which most trolls and later Doopie herself recognized as Chris attempting to hit on a potential Sweetheart. Chris's incessant use of the term was a key factor in making Doopie feel uncomfortable with interacting with him and setting the stage for the climax of the Doopie Saga.
Chris later brought the term back, along with "dear", when interacting with Doopie's friend LadyOfTheCosmo, who turned out to be much less tolerant of it than Doopie. She tried to convince Chris, to no avail, of the typical connotations of the words, only resulting in Chris obstinately continuing to address her with them. Lady's patience with this unraveled rapidly to the point of simply cursing at Chris, before he unfollowed her and she blocked him. Chris then used his sockpuppet account to roleplay the "proper" use of the term.
He has also used it on Tabitha St. Germain.
Chris uses both "darling" and "dear" to refer to his mother. His MLP-inspired character of her is named Sugar Darling. He is heard addressing her as "dear" in an April 2017 Captain's Log, and Clare Porter has further mentioned that he addressed Barb that way over the phone.
Chris thinks that his use of the term is justified as the late actress Tallulah Bankhead used it liberally in movies. He wrote about this in a letter addressed to LadyOfTheCosmo. However, what Chris fails to consider is that unlike himself, Bankhead was an attractive woman who only used the terms as such while on set.
|Open Letter transcript|