- Edgar's PTSD includes one Noodle Incident that is referred to in a dark Running Gag during the second season: "I didn't know it was a school."
- Overlapping with Tear Jerker, Gretchen's depression/mental illness is portrayed with terrifying accuracy. While many works focus on the "sadness" element of depression (and there is plenty of that at the beginning of her breakdown, sneaking out at night to go cry in her car), the show goes beyond that and addresses the stage of feeling nothing.
- When a group of female gang members attack her, Lindsey, and Sam's group, Gretchen remains completely deadpan as she points a gun at one woman's head and simply says, "Run." She later tells Lindsey that all she felt was bored. It's chilling.
- In "LCD Soundsystem", Gretchen is so unstable and desperate to feel something that she tries to copy the life of a couple that looks perfect to her. Complete with walking out of a store holding their child and later stealing their dog so she can pretend to be normal and get into their house when she returns him. The episode ends with the revelation that said couple has a ton of problems, followed by Gretchen and Jimmy walking home as she starts crying.
- Black Comedy to the extreme when Edgar goes to ask Paul for permission to "court" Lindsay. Paul gives a truly disturbing description of how his friend Connor's wife recently died. She was run over by a semi truck while riding her recumbent bicycle and was dragged three miles underneath it, and apparently kept texting Connor until shortly before she died.
- Though played entirely for laughs, the haunted house in "Spooky Sunday Funday" was nothing short of horrific. Loads of blood, mangled animal statues, and disfigured people roamed the place terrorizing everyone there (minus Gretchen, for the most part).
- Whatever the hell is going on with Killian. He's 12 or 13 years old, lives alone in his house and his only support system is Jimmy, Gretchen and Edgar. Jimmy abuses him verbally and uses him as a odd job man - a bartender and a typist for Jimmy's writing (which appears to be at least soft-core porn, no less) among other things; Gretchen seems to just ignore him; and Edgar seems to not notice him until Killian addresses him directly. Killian clearly has no means of support, and his only source of food is what he can beg or steal from the protagonists. Each of the protagonists has, therapeutically speaking, a mountain of issues - if he lives to adulthood, Killian's going to have a whole mountain range of them...
- In "It's Always Been This Way", Vernon, who's been exhausted from doing the bulk of the work in taking care of Tallulah while Becca's been turning towards drinking, passes out in the middle of doing a surgery and accidentally cuts a major artery open in the patient he's operating on, spraying blood everywhere.
Nightmarefuel / You're the Worst