Cyndee's idea of dates seems based on media from The '50s. While pretending to be her boyfriend, Kimmy mimes using a column-mounted gearshift, which were common in the Fifties, to match the setting.
Part of the joke of Titus singing Boyz II Men's "I'll Make Love To You" at a funeral might be that it would have been less awkward if he had only thought to perform a different song by the same artist: One of their other hits is the Mariah Carey collaboration "One Sweet Day", which is a Grief Song.
Kimmy's overly colorful wardrobe reflects the fact that her fashion sense hasn't evolved since she was 14, but might also be a reaction against her time in the bunker, where she was made to wear drab, floor-length dresses.
At one point Kimmy greets the Vorhees' Mexican housekeeper with a cheerful "Cállate," which the subtitles helpfully translate as "shut up." This is probably what Donna said whenever she walked into a room, especially considering Kimmy's Motor Mouth.
Some of Kimmy's word choices subtly refer back to her lack of formal education since her early teens. For example, she says "tooken" instead of "taken", "lookit" instead of just "look" and "how come" instead of "why." Cyndee, who was also taken at a young age, does the same.
"Kimmy Kidnaps Gretchen!" has a gag where Gretchen pronounces Steve Buscemi's last name "Busk Em Eye". By 2004, the year Gretchen was kidnapped, Buscemi was a fairly well-known actor and had already made some of his best-known films, such as Reservoir Dogs and Fargo... But Gretchen not being very familiar with him still fits her background, since most of those movies were rated R and thus unlikely to be watched by an 18 year old note If Gretchen never got to see an R-Rated film prior to being in the bunker, pretty much the only movies she could have seen Steve Buscemi in would be Armageddon (1998), Big Daddy, Fargo, The Wedding Singer, or Billy Madison, all rated PG-13 and released in the mid-to-late 90's. Alternately, it's possible she's seen his name in print before but never heard it spoken aloud.
The events that complicate Jacqueline's quest to change the name of the Washington Redskins are Iktomi's doingnote For reference, Iktomi is a spider trickster spirit of the Lakota People. Throughout season 3, Jacqueline believes that Iktomi will help her succeed, until she learns that Iktomi is a deity she wouldn't want on her side... given that he is described as a trickster, it makes sense.
Kimmy complains of Cyndee’s sensitivity, saying even Donna Maria in a fake moustache made her cry. An earlier throwaway gag shows Cyndee was the only Mole Woman to learn any Spanish, so only she knew how mean "Don Mario's" jokes were.
Episode 1 when Kimmy admits to Titus that she's one of the Indiana Mole Women:
Titus: May I ask a question — Kimmy: [as if sick of being asked] Yes, there was weird sex stuff in the bunker!
Kimmy was fourteen when she was kidnapped. The horror multiplies when you realize that this line was written by Tina Fey, whose face was slashed by a knife-wielding stranger when she was playing in her front yard as a five-year-old.
Kimmy: The worst thing that ever happened to me happened in my own front yard.
Kimmy: I had a weird childhood (she says after hitting a guy she's about to have sex with a telephone - twice.)
Kimmy also has a variation of Hates Being Touched, if she doesn't see you or know who you are and you're closing in on her, she will freak out and start throwing fists. What happened in that bunker?
Could also be what happened to her when she was kidnapped in the first place. Despite her sunny attitude, she's terrified of it happening again.
Kimmy's nightmares, which include flashbacks and physical violence which she rarely seems to remember upon waking. (The one from which she wakes up while cleaning a knife clearly terrifies her.)
As shown when Kimmy and Logan try to have sex, Kimmy's has an idea of what's normal in bed that's not just odd, but also disturbingly violent.
One of Xanthippe's friends mentions that her boyfriend is a married man and another time that her doctor is in love with her. She can't be older than 16, so if the relationships do actually have any physical component to them, she'd be a victim of statutory rape. Even in the case she was lying about it, it still gives the horrific implication that being in such relationship is seen as positive in her social group. Similarly, Xanthippe's flippant reference to one of her dad's adult male friends giving her jewelry in exchange for her old retainers, which is squicky on several levels.
The senile old man Kimmy goes on "dates" with to share dark secrets eventually mentions that he pretended to be his brother so he could sleep with his twin brother's wife. In many places, this would be considered rape by fraud.
Or, perhaps alternatively, who he referred to as his brother's wife was actually his and he's just too far gone to realize it.
Jacqueline's husband's control over her, while not named, is a form of abuse called gaslighting. Complicit in this is Jacqueline's own marriage counselor, who's positioned like a therapist.
A running gag in Season 1: Kimmy is terrified of Velcro. Hilarious, random gag, right? In Season 2, we find out she was struggling with Velcro on her shoes when the Reverend emerged from a dark van and took her into the bunker. Oh.
A couple, regarding Cyndee’s “relationship” with Brandon. Firstly, Cyndee knows that Brandon is gay and is only with her out of pity over Cyndee’s ordeal as a Mole Woman— this darkly parallels how The Reverend kidnapped Cyndee by luring her to his car which she allowed out of a fear of being “rude,” in other words, Cyndee and The Reverend both took advantage of societal expectations and pressures to manipulate Brandon and Cyndee into a situation they didn’t want to be in. Secondly, there’s the strong possibility that Cyndee’s determination to be with a man she knows is gay is subconsciously driven by trauma over the years she spent as at the very least a witness to (if not also a victim of) The Reverend’s sexual abuse.
In season 4, we find out that one of Titus's more recent gigs is doing stock footage for what later turned out (or rather gradually turn into) an MRA documentary slamming Kimmy and the other Mole Women, which he was also surprised at. Which is strange because one of the shots is obviously Titus pretending to be Kimmy in the bunker, yet he somehow didn't pick up on. I know this is supposed to run on Rule of Funny, but even by Kimmy Schmidt standards, it seems rather odd that they wouldn't notice that.
It does rather fit Titus as a character to be too self-absorbed, and too keen on keeping what was an easy paying gig, that he wouldn't think to, or necessarily want to, ask any inconvenient questions. After all, it wasn't his reputation on the line.
