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This is a "Wild Mass Guess" entry, where we pull out all the sanity stops on theorizing. The regular entry on this topic is elsewhere. Please see this programme note.
Daria
Beavis And Butthead do not exist in the Daria's universe spin-off
A very plausible theory, as it is very curious that, throughout the series, Daria never mentioned the duo. Interestingly, Quinn never appeared on Beavis and Butthead, either. But what really makes it even more plausible theory is that Daria actually had some plot progression and the show even ended with Daria and her friends splitting up and going off to college. Meanwhile, Beavis and Butthead have been in the same grade with the same teacher and classmates for well over 15 years at this point.

Charles "Upchuck" Ruttheimer III is related to Beavis and Butthead
Note that all three have similar aspects, such as physical appearance, nose and the Casanova Wannabe personality. Upchuck may be the cousin of either of these two. The only difference is that, compared to Beavis and Butthead, Upchuck is a genius.

Tom Sloane died by the end of the episode "Is It College Yet?"
Note that after the last conversation between him and Daria, he would never be seen again onscreen, not even was seen talking on the phone with Daria in the last lines of the episode. Maybe he was hit by a car, maybe died in a car accident, whatever, the point is that he died. And it is very likely that Daria and Jane know that he is dead, see when Jane says that he was "recycled" and Daria says that Tom is currently on a secret mission, and probably metaphorically said if you think about it, is very reasonable that this "secret mission" is referring to what he is doing his soul after his death.

Trent had feelings for Daria, but thought she was too good for him
Trent clearly had a high opinion of Daria. He was also very insecure about his own "career choices" and his future. He didn't really have the maturity to handle it, so he acted like he was ignorant of her feelings, not realizing that that would hurt her.

The music that played in the background of the original version of each episode is the music Daria had stuck in her head at the time.
Note: The music was almost completely rewritten for the DVD release, so this does not apply to that — though the songs on the DVDs reflect the spirit of the originals, so maybe the theory can still work for them.

Daria, an MTV production, used songs that were recent at the time of airing as background music...

The entire series is written by Daria herself
It would explain why Brittany and Kevin are so dumb, Ms. Lee is so evil and bureaucratic, why Helen and Jake are so embarrasing, why Quinn etc.
  • However, if Daria was writing them, the popular people would not be popular. She would write something that really makes them suffer.
    • Or it could just be her interpretation of the events after the fact. She might exaggerate things to fit her own interpretation but she wouldn't outright change the outcome. Plus I wouldn't be suprised if Daria saw the world as the popular people always win and her always losing/life just passing her by. She's not writing a fix-it fic about her life but a recording of the events from her own point of view.

The Episode "Depth Takes a Holiday" is a daydream of Daria's
  • It's basically a bizarre daydream that Daria is having. The Holiday Spirits are also a part of her Wish Fulfillment for people who might actually appreciate her. This is helped by the fact that they say that she is cool and the only one who can help them.

Sandi is a M-to-F transsexual
  • Thus her deep voice, highly aggressive attitude and extreme bitterness and resentment towards Quinn, the beautiful teenaged girl she wants to be.
    • Aw, that would make her sympathetic.
    • Intriguing as that would be, you can't go on the drugs and have the surgery that allow that until you're through puberty. So if she is a transwoman, how does she hide her external genitals?.
      • Yeah, no, actually — there are plenty of transwomen who transitioned before puberty.
      • Ah, the sacrifices we make for fashion.
      • Tucking. Learn about it.
      • That would be hard to do all the times the rest of the fashion club has seen her in underwear or a bikini.

Quinn is a M-to-F transsexual
Similar to the theory above but would actually seem more plausible given the fact that the high pitched voice Quinn has sounds so fake and Quinn engages in interests involving the feminine gender stereotype and image. It also explains...

  • Sandi having such hatred for Quinn and trying to ruin Quinn's social life.
  • Quinn's desire for acceptance. Being "attractive and popular" is validation of her passing as female. Why else does she keep asking her dates as well as any guy she likes if they find her cute?
  • Quinn getting squeamish on her dates with guys, she doesn't want them to find out.
  • The family moving from Highland to Lawndale to start over. (If you were Helen, would you want your transgender daughter around the likes of Beavis And Butthead?)
  • Quinn's issues revolving around her pores and cheese on pizza are because of they way that interacts with her hormones and testosterone blockers. With Helen being a lawyer, she'd find a way to get her kid some hormones.
  • Quinn acting like Daria isn't related to her for her paranoia over people knowing that Daria is related to her, then people will ask about Quinn's past and thus out her. Daria isn't above blackmail and bribes.
  • The way that Brooke's plastic surgery got Quinn in a frenzy.
  • Helen's concern about the way Daria would portray Quinn in that video project.
  • Jake's trauma of being tormented by his father by not being manly enough, and it instead of it being for laughs is really the anguish of a father accepting that his son has become his daughter and his hard time coping with that.

Quinn is asexual.
Exactly What It Says on the Tin. She enjoys being attractive and popular, and gets a sense of self-worth out of boys paying attention to her, flattering her, and fighting over her, but she's just not interested in sex. With the amount of time she spends winning boys over and then pushing them away when they get touchy, she might be aromantic as well.
  • Glenn Eichler stated in regards to the main characters sexuality Quinn hasn't gone that far because she's more interested in status and what gifts she can get than actual physical affection or pleasure.

The Lane kids murder their parents off-screen at the end of the episode "Lane Miserables"
  • This secures the house for Jane and Trent to live indefinitely, and gives them money to live off of from the life insurance.
    • Jossed in a "Art Burn" where they have to rebuild the porch thing that fell apart in the backyard. The parents are seen at the end of the episode, alive and well.
      • It's called a Gazebo, now you have angered the gazebo, smooth move.

Daria and Jane are lovers
  • At least until Tom comes into the picture, which explains why Daria was so angry about him and Jane's relationship.
    • A popular myth explicitly Jossed in Is It Fall Yet?. Daria and Jane are good friends, but nothing more.
      • But this doesn't preclude some pre-IIFY experimentation that they no longer talk about. The experience may even be why Jane was sure she was straight and could say so firmly.
      • Glenn Eichler stated he intended Jane's sexuality to be a question mark - Is It Fall Yet may have made Jane realize she's bi, closeted, or at least curious, but he was firm on Daria being straight. Word of God doesn't mean anything with Wild Mass Guessing, of course, just putting it out there.

Daria is in love with Jane
  • Daria's crush on Trent was her trying to redirect her attraction to Jane onto a more socially acceptable target, but one who still resembles Jane. When Tom came along Daria was understandably devastated and initially hostile towards him, but was ultimately drawn to him due to him being associated, in her mind, to Jane.
    • Resembling Jane? Jane does not take naps all day, nor speak so slow
      • There's a pretty strong physical resemblance, though.
    • The reverse could be true-Trent is redirecting romantic feelings for Jane onto Daria.

Alternately, Jane is in love with Daria
  • Think about the guy she ended up dating: Intelligent snarky brunette with a taste for classic literature. In other words, just like Daria. However, choosing a guy just like her best friend came to bite Jane in the butt as Tom and Daria were enough alike that they eventually fell for each other.
  • I guess you have missed Is It Fall Yet?. Jane rejected that idea explicitly. And she did not miss chances to flirt with other boys earlier, as in "See Jane Run".
    • Many lesbian and bisexual women insist that they're straight and date men exclusively, before coming to terms with their sexuality. Considering how shaken Jane was by Alison's belief that Jane was gay, it's entirely possible that Jane is in denial.
      • Note the painting she does after Allison's failed seduction is of herself screaming in a closet.
    • It may be a subconscious thing.

All the inhabitants of Lawndale are immortals
  • The images that play over the credits actually did occur in the past.
    • Doesn't explain the ones that are of animals or even inanimate objects, or the ones that obviously parody real historical figures or characters that are fictitious even in the Daria universe.
      • They took the next leap
      • Does this mean that Daria and Jane have to go to High School and cope with vain and dumb people for all eternity?

Daria is really Aunt Amy's daughter
Amy inadvertently got pregnant, but decided that she wasn't ready to raise a child, so Helen and Jake, who were already married suburbanites at the time, offered to adopt the child. Come on, Daria is the spitting image of Amy, and a very similar personality-wise.
  • They're even the only ones in the family to wear glasses, and the need for glasses is genetic.
  • This would mean that all this time Quinn was telling the truth about Daria being her cousin.
    • It also makes sense in the first episode when Daria overhears Quinn telling a guy that she's an only child and gets angry. She's pissed that Quinn doesn't see her as a real sibling.
  • This might also help explain Daria's alienation from her parents, and why her mother often punishes her instead of Quinn, since she doesn't want to treat Amy's daughter better than her own.
    • We've seen that Helen has a lot of rage towards Rita. Maybe she doesn't have that level of frustration towards Amy because she takes some of it out on Daria.
  • In all seriousness though, there are plenty of people who like more like their aunts and uncles than their own parents. Genetics are funny that way.

Tom Sloane is not very popular at his school
  • Despite his belonging to a wealthy, old family he drives an old car all the time and his family has a bit of a reputation for not doing anything exciting. He is very intellectual, and doesn't seem very interested in his own social class. When Daria tells him that a rumor is going around Lawndale that the two of them had sex, Tom asks "jokingly" if they could get the rumor going at his school, too. In one episode his "good friends" blow him off. We learn very little about Tom's own school life, but it certainly looks like Tom wasn't a very popular guy on his home turf.

Rock and Roll Randy was the husband who divorced Ms. Barch
  • It does explain why she screamed, "It's payback time now, Randy!" as she's punching him in the stomach during that roller hockey game as seen in "The Big House" (the episode where Jake and Helen start a "Family Court" after Daria and Quinn each get in trouble for coming in after curfew). It couldn't have been because she was defending Mr. DeMartino, as later episodes like "The New Kid," "The Daria Hunter," "Murder She Snored," and "Is It College Yet?" reveal that Ms. Barch hates Mr. DeMartino (as she does all men, except for Mr. O'Neill) and takes out all the aggression she has over being divorced on DeMartino.
    • "Janet, please, don't think me forward or randy by asking you this, but..." Fridge Brilliant Stealth Pun?
    • Hmm, knowing Ms. Barch I think she more likely meant, "It's payback time now, Randy...for everything your lying, selfish, philandering, misogynist sex has done to womankind since Eve came from the rib! I spent twenty-two years cleaning his whiskers out of the sink and it's YOUR stomach that's gonna pay for it, you...you MAN!" Besides, it's hinted (heavily) in "The Daria Database" that Ms. Barch's ex wears "cheap, tawdry designer shirts." Doesn't sound like Randy to me.

DeMartino is related to Principle McVicker
Mainly due to their simmularities. Besides, wouldn't that be awesome?

Daria's favorite band are the Deftones.
Come on, it just sort of makes sense. The era (late 90's - early aughts) is right, and they totally sound like the kind of band she would listen to. She seems like the kind of person that would enjoy a band that combines elements of alt rock, dream pop, post metal, and new wave.
  • Considering that Daria spends a lot of her time reading, one would think her favorite band would have some sort of Heavy Mithril elements in their music. Perhaps something like Bal-Sagoth would be up her alley.
    • Eh, I doubt it; in this troper's expereince, lit nerds listen primarily to Godflesh, Neurosis, The Smiths, My Bloody Valentine and Deftones.
      • More probably, Daria simply does not care about music.
      • A character on TV show on MTV that was spun off of another show on MTV has no opinion on music what-so-ever? In the 1990's when they still played music videos on MTV?
      • Well, yes. She was even temporarily in love with a guitar player, and hardly ever made a comment about music. Not even on the way to Alternapalooza. As for New Metal and similar stuff, she once defined edgy as "As far as I can make out, edgy occurs when middlebrow, middle-aged profiteers are looking to suck the energy — not to mention the spending money — out of the "youth culture." So they come up with this fake concept of seeming to be dangerous when every move they make is the result of market research and a corporate master plan."
      • Lots of people don't "like" a particular band or artist, instead simply picking and choosing the music on a song-by-song basis. I'd say though Daria likes music, but she's not one to say "X band is the best!"

∆on Flux is a descendant of Daria, Jane, or perhaps both.
No real reason, other than it would tie it in to the rest of the MTV Animation-verse. She does have a similar sarcastic monotone voice, at least...

Upchuck is Archie Andrews.
Perhaps an alternate-universe version or something. Or perhaps this is the real Archie and Archie comics is just his fantasy life.

The full name of "Mystik Spiral" is actually: "Mystik Spiral, but we're thinking of changing the name"
This is why they introduce themselves that way most of the time; "Mystik Spiral" is just a diminutive form of the name
  • Mystic Spiral end up getting their big break by opening up for Dethklok
  • And one of those shows on said tour will bring forth the Metalocalypse. Fittingly, Daria and Jane will mock the carnage and senseless violence around them.

Tiffany is Alan Rickman

Or at least Alan Rickman playing Snape. Hence... the awkward... pauses.

Mack would have played Tom's role and been involved in the Love Triangle with Daria and Jane if the producers had found a stable voice actor for him and got to use him more like they wanted.
One of the main complaints about Tom was that he was brought in out of nowhere simply to act as a plot device to set up the love triangle story arc and that it would have been better to use an established character. Out of all the teenaged boys in the regular cast before Tom's introduction, Mack would have fit the bill perfectly. It's hinted several times, especially in the books, that his relationship with Jodie is shaky, he's at least sympathetic towards the girls and closer to their intellectual level than any other recurring male character their age. The only thing stopping them was the notorious voice actor issue relegating him to background status.
  • And where does that leave the poor old Jodie? More than a love triangle, it would be a Love Dodecahedron, or even an Unwanted Harem. Too much for a character that hardly ever managed to say something.

Daria takes place in the same universe as Becker.
There's this episode of Becker (Old Yeller I think) where he encounters this really sarcastic girl in glasses. Everything about her, even her voice, reminds me of Daria.

Daria has a touch of autism
Come on. She's very smart, just not very good socially. The obsession in "Boxing Daria" is classic.
  • The most common theory is Asperger Syndrome based on her actions, interests, and interactions with other characters.
    • Speaking as an Aspie, I disagree. It's not so much that Daria is socially inept — she's clearly made a deliberate choice to be antisocial, because who wants to be social with idiots like Kevin and Brittany in the first place? She chooses to avoid the stupidity around her, that's not the same as the kind of social awkwardness and inability that autistic people have.
      • If I remember correctly, there's a blink-and-you'll-miss-it line in "Boxing Daria" where she mentions that the few times she did attempt to socialize they couldn't understand her and just started making fun of her, the implication being that she just gave up after that happened one too many times. That's actually something very familiar to a lot of us.
  • The problem is that disorders such as autism and Asperger's are impossible to get a feel for in fiction absent them being intentionally written that way and only Word of God can do that. Being a high function autistic I can see how you could make the case but telling a difference between someone who is antisocial by choice vs someone who lacks the skill due to a disorder can be a very iffy line even when you have an actual living person to diagnose.
  • Another Aspie here. I would argue that Daria displays more than enough aspects for Asperger's syndrome to be a believable possibility, to the extent that that can be said about fictional characters; her signature monotone, her introversion, Her disconnection from the people around her, her limited social circle, even her limited wardrobe. Every line out of young Daria's mouth in "Boxing Daria" sounds like an example out of an Asperger's textbook. Her reluctance towards sex, "the thought of that much intimacy is just overwhelming to me", sounds very much like Sensory Overload. Granted, all of these on their own don't an Aspie make, but put it all together and you've got a pretty strong case.
  • Every line in that entire episode sounds like something from a traumatic memory from the early childhood of someone with Asperger's, HFA or PDD. I'm weighing in as a specialist in the Autistic support field who grew up with Asperger's, and has literally met and worked with hundreds of kids on the Spectrum. The problem with diagnosing a fictional character, however, is that even in shows with relatively strong continuity, characterization can change from writer to writer, episode to episode. From personal experience, I can definitely say however that there was a certain point when I was seven that I decided other kids were not only not as intelligent or articulate as I was, but that they were mostly assholes and I didn't want to be like them at all — especially the popular kids, who played sports and enjoyed gym class. In typical Aspie fashion, I felt very, very strongly about this, like a moral commitment, and I proceeded to do weird things that made me even more of an outcast than I already was... very much like young Daria probably felt. She had early difficulties with socialization, which eventually reinforced her decision to withdraw from people to whom she really couldn't relate. Later, as she matured, she overcame some of these social barriers while maintaining her integrity (her friendships with Jane and relationship with Tom being good examples of this, as well as her eventual recognition of a spark of intelligence in her sister, Quinn, to whom she actually offered romantic guidance in "Is it Fall Yet?")
    • This Troper does not feel that the knowledge that you are more intelligent and articulate (and a nicer person) that many of your "popular" peers from early grade school, and the subsequent isolation and vicious cycle is necessarily a sign of being along the Autism spectrum, because former classmates of mine and I, not along the Autism spectrum, had similar experiences at that point in life. Children along the Autism spectrum, or with learning disorders of any kind (I personally have significant dysgraphia) are more vulnerable to early exclusion and rejection from "popular" groups, but part of it is just the nature of athlete-centric and performance-centric social groups that form among youths.
  • Daria having an anxiety attack in "Ill" supports this theory.
    • She was nervous around the guy she had a crush on. The stress of appearing vulnerable and NOT badass and tough around her dream guy is a reasonable explanation to why this happened.
  • As someone with Aspergers, I can actually see a lot of myself in Daria (though not as cynical), particularly as a child, so I could believe she has it. That said, I strongly believe Quinn could have it as well; uncomfortable when physically near several members of the opposite sex (at the school dance), a desire to fit in, and wanting to feel like she can be a better person are some strong traits I believe could be associated with Aspergers in females. Perhaps when her character arc kicked in during season 4, that's when it started to really develop.
    • As ANOTHER person who is on the autism spectrum, I'm not seeing it. Daria is misanthropic, intelligent, doesn't like people, and is arrogant (not that she's a bad person, just a bit of a snob at times with her intellectualism.) The main trait of autism is social ineptness. When "forced" to socialize, Daria is very good at this — she's socially savvy. She makes a deliberate choice to isolate herself, as she believes that her brains make her superior to others. She isn't socially awkward — in fact, she's the OPPOSITE. She understands everyone and can read people like books. She always knows exactly what to say in any situation.
    • Also, Daria mentions (and shows through her behaviours) that she is very clear on exactly how she could be popular, but is making a deliberately calculated choice not to be. To put in another way, Daria is as aware of fads and trends as any other girl, she just follows fashion in her own way: by deliberately staying as far away from it as she possibly can.

Daria and Jane are dead
And they are in hell, where the Devil is punishing them for being so ironic... by forcing them to go to Lawndale High all over again.
  • Ironically, in the 2011 Beavis and Butt-head episode "Drones", Beavis believes Daria committed suicide. If it wasn't for Butt-head to mention she moved away, many people would believe that Beavis was right, Daria's dead, and Lawndale is her hell.
  • But that's Beavis & Butt-head, they are not exactly reliable. In fact, if Beavis says that Daria commited suicide, the most logical thing to happen next (if copyrights were not an issue) is that Daria appears at his back "Hello, losers! Long time no see... how I wish it was a longer time"
    • It would be funnier if an adult Daria somehow ran into the still 15 year old Beavis and Butt-head and said "How the hell are you guys still 15?" Not only would it point out the fact that the Beavis and Butthead has negative continuity but also it would play into the "Uranium in the drinking water" joke from the first Daria episode.
Daria slept with Beavis And Butthead
Ok here me out, the very first episode of Daria involved her moving to a new town. The last episode of Bevis and Butthead before their revival in 2011 featured them leaving Highland. Sometime before the pilot they ran into each other make fun of each other on their own expense and well... My evidence of this guess is what follows:
  • While she Initially hated them at first, she was willing to help them get straight As for their science project.
  • She is one of the few characters willing to seek them out that didn't intend to kill them off.
  • In the Christmas Special it was stated that they were actively responsible for making her less expressive and more of the Snarker we know and love in her own show.
  • Despite her views on the world she was never driven insane by them.
  • Lastly because while they mutually make fun of each other and forget about each other aside from a few references to their respective shows. They were the first ever to acknowledge their respect for one and other, despite their idiocy and her sarcastic view of the world.
    • Citing Daria, do you really picture her sleeping with... anyone?
  • She could have done something sexual with one or both of them. Could be an Old Shame/Skeleton in the closet she'll never talk about.
    • I wouldn't put it past Beavis and Butthead finally scoring and not remembering, or better yet they didn't count her as scoring.
  • She seemed violently defensive about it during her Dear Daria days, whenever asked about shipping her with one or both of them.
    • Wouldn't you get violent if you were shipped with them?
  • Daria had more respect for Beavis and Butthead than any of the other kids are her school because those two had no choice but to be ignorant and stupid, whereas all the other kids were purposefully avoided learning and improving themselves because they were trying to conform.
Mr. DeMartino is Inspector Zenigata from Lupin III
  • They sound similar, plus they are both very high strung.
Tiffany is a Drug Addict.
How else did her voice change from a sarcastic snob to the slow talking girl we know now?
  • Probably her parent's prescription meds.
The Griffins are related to Carrie from The King of Queens
  • It's pretty simple, Arthur spent some time in Lawndale and got a woman (Sandi's grandmother) pregnant then skipped town, eventually settling down in New York, getting married and fathering Carrie. Not only do Sandi and her mother look just like Carrie they are all aggressively obnoxious, self important and self centered, and the time lines even fit together, a general estimate puts Sandi's mother at 10 to 15 years older than Carrie, more than enough time for the events to have happened before Arthur got married.
Mrs. Barch now O'Neil
Will end up having a son. Karmic punishment for all her man-hating.
  • God, I pity that kid.
  • Alternatively, she will realize that the son is the product of her and Timothy's relationship built on love and respect (at least, a better relationship than what she had with her ex), and she won't raise him with hate.
Daria is really a genderswap of Fight Club
Daria is the narrator, Jane is Tyler Durdan, Trent is Marla.
At the start of the series, Jane is an out-of-control party girl.
It's easy to assume Jane's in the self-esteem course because she's antisocial, but what if she were placed there because her social life is taking her down the wrong path? Even though he calls her his kid sister, Trent is really close to Jane. It's easy to imagine him getting her into over-21 clubs, taking her to gigs in skeevy locations, and introducing her to his soft drug connections. In the first season, Jane's humor is cruder and she isn't as quick-witted(think of the time she says selling chocolate makes her feel "the bad kind of dirty," for instance). The first season has Jane making out with a stranger in a laundry room and jumping at the chance to go to Alternapalooza, even though she doesn't seem to have much interest in music. Her grandmother screams "What the hell is wrong with you?" in her face. Later Jane is much less impulsive and seems to take better care of herself, if her voice is any indication. By comparison, Trent seems to get slower, less ambitious, and even less interested in his music as the series goes on—perhaps because he no longer has his best buddy Jane around.

Daria, song along with other characters, are magical girls, or boys in some cases.
Long before the move to Lawndale, Daria and Quinn made wishes, which caused chain of events that led to what Lawndale is now. Quinn wished to get away the pain of Highland Daria wished to be more popular. Jodie could have wished smarter classmates, Jane for a best friend, Trent for Parental Substitute, and so on.note  I wrote another Madoka Magica/Daria crossover WMG on ''Madoka Magica'''s crossover theory page (that page contains MEGA spoilers, so read at your own risk).

Daria and Quinn were raped by Beavis and Butthead.
Beavis and Butthead are desperate to score, and Daria was the only who would socialize with them voluntarily. Realizing that they would probably never score, they lost control of their impulses. This is why the suddenly Morgendorffers moved out of Highland. Quinn subconsciously blames Daria for the rape, which is they donít along well.
  • Do you really think these guys have the attention span required to rape someone?
  • If Beavis & Butt-Head tried this, they would not fare any better than they always do: a slap, a punch, or a kick in the groin; end of story. Daria goes away, and the duo stays in the ground filled with pain. Not even Tinker Bell may be raped by those guys.

O'Neill has prosopagnosia
Prosopagnosia, or face-blindness, is the inability to recognize and distinguish faces. Mr. O'Neill frequently appears to have considerable trouble putting student's names to their faces. In "Through a Lens Darkly" he didn't recognize Daria simply because she had her glasses off—people suddenly changing what had been a consistent facial feature makes them hard or impossible for a person with prosopagnosia to recognize.

Wealthy Lawndale's school budget problems are tied to Fielding Prepratory School
The truly wealthy families probably sent their kids to Fielding Preparatory Academy (Where Tom Sloane goes), and the "peons" of middle wealth go to Lawndale with its budget problems. The wealthy parents (in the majority) probably have some system to keep from having to pay Lawndale school tax that they manahged to push through council, adding to the budget problems. Mrs. Li is driven batty by parents complaining about the school's budget and the meager allowance she gets to work with as the richest and smartest students are selected and bribed go to Fielding. Her wacky budgeting is due to years of this, and she's cracking.

Daria is a fob-watched Time Lord.
Leaving Highland is just the backstory. The reason she wants to sit in the box in "Boxing Daria" is because of buried memories of her Tardis.

Trent is a Shipper on Deck for Jane/Daria.
Not in a creepy way, in a "I want my little sister to be happy" way. Daria is more or less the only friend Jane has at Lawndale, next to maybe Jodie. Trent clearly loves Jane, and clearly wants her to be happy. Perhaps he saw some Les Yay subtext and thought, "Oh, cool, my sister is finally in a good relationship." Notice that when the girls fight, he's often the one to nudge them back together.

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