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"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.

Chris used this term as a 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.

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.

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