* Helen's BreakTheCutie moment in "Psycho Therapy": ''"Everybody hates me."''
** And unfortunately, Jake and Helen weren't exactly wrong with how they were portraying each other. Jake uses his DaddyIssues to avoid responsibility, and Helen does have a tendency to act like ItsAllAboutMe. "Lane Miserables" opens with Helen making a big deal about how families should spend time together and feels the need to bring up how she had to rearrange numerous meetings that could impact future dealings so she could be there. She then wonders aloud why she even bothers when no one acknowledges what she just said.
* In the episode where Quinn becomes obsessed with what she believes is her guardian angel, she has a crisis of faith and asks Daria for advice. Daria takes the blunt tactic of simply stating that until proven otherwise, she doesn't believe in any afterlife. Something about the way Quinn says "But... that's so sad..." is just heartbreaking.
* When Quinn's tutor rejected her and she began to cry in Daria's room. It was the first time she actually really ''liked'' someone, and for more than superficial reasons. For the first time in her life of guys blindly worshiping her, she gets rejected. It was one of her rare moments of genuine vulnerability to a guy.
* "Boxing Daria", the entire episode. The sight of an over-sized refrigerator box causes Daria to [[RepressedMemories recall parts of a childhood memory]] of her in bed, overhearing an argument between her parents and her dad storming out. This memory keeps nagging at Daria and leaves a real strain on her, until she finally remembers what the argument was about: Jake and Helen were fighting about her, due to the collective stress of working aggravating jobs ''and'' being called in by the school because Daria wouldn't socialize with the other kids. The box was important [[SecurityBlanket because Daria had one just like it when she was younger that was a sort-of haven.]] The entire episode has Daria on the defensive and very insecure, and even the normally flighty Quinn is rather unnerved. Seeing her be that emotionally vulnerable without bursting into tears and thinking that she's a cause of constant and unwarranted stress on her parents and family because she chooses not to socialize and "be herself" is almost painful. This is something that just about everyone has gone through in their life, and it's hard not to sympathize with Daria and be a little awed by her when you realize she began to reconsider the decisions she's made and wonder if she may have been wrong in making them the way she did.
** It also hits ParentsAsPeople hard at home too. Turns out that while they did have a fight about Daria's problems in school; Jake and Helen were struggling working bad jobs they had to work and all the petty stresses just exploded with Daria being the final straw. Daria takes it all as her fault (and given the fight at the time, it's perfectly understandable). Jake and Helen were completely over-stressed and took it out over their child. While not right to do; its not uncommon for people to well up and explode.
* In "I Loathe a Parade", Tom and Jane head off together, leaving a paint-splashed Daria behind. Tom steals a longing glance back at Daria, who fades into the distance looking utterly lost.
* The end of "Dye! Dye! My Darling". After "The Kiss", Jane tells Daria that she and Tom broke up, and then they argue about the events leading up to that point. At the end, they break off their friendship (at least until "Is It Fall Yet?").
** That whole episode is full of depressing moments. From Jane forcing Daria to dye her hair which is very clearly an excuse to pick a fight, to Jane and Tom breaking up, to Daria's incredibly out-of-character sadness and urge to talk to her mother about it, to Daria telling Jane she and Tom kissed and Jane getting so mad at her.
* There's something incredibly tear jerking about Kevin and Brittany's implied separation in "Is It College Yet?", probably due to the fact that out of all the relationships in the show, theirs was always the closest and the happiest.
** One still feels sad for Kevin, who is left behind by his classmates in high school and then by his girlfriend.
** And let's not forget about Daria's break-up with Tom. Even Daria herself is genuinely heartbroken of that choice.
* In "See Jane Run", Jane joins the track team and becomes a big athletic star. Daria talking to herself is funny until it hits you that she's doing it to compensate for Jane being busy with practice all the time. Jane is her only real friend in the world, and not seeing her really takes its toll on Daria.
* In "Is It Fall Yet?", Daria has finally made a bond with the outcast boy at the summer camp she is volunteering at. He starts to open up to her, so that she can help him... and O'Neil comes waltzing up and interrupts, making Daria's attempts at friendship sound more like manipulation. Incensed, Link storms off, followed by Daria, both looking like they want to cry at how everything went wrong in a matter of seconds.
* In "Write Where it Hurts", Daria is frustrated about her inability to complete a writing assignment. Helen, after initially upsetting Daria due to her own stress problems, helps Daria to come up with a writing premise. Just hearing Helen speak so knowingly about Daria, which indicates that she cares far more than Daria realized, is touching. But the real kicker is the story itself: [[spoiler:She writes about her family, years in the future, happy and well-adjusted. Her sister is raising a family, Daria's a professional writer, her father is much more relaxed and her mother is content. Underneath all the layers of cynicism and sarcasm, she loves her family and wants what's best for them all]]. Helen wasn't the only one tearing up after she read that.
* In "Lane Miserables", Trent says he once lived in a tent in the yard for six months, waiting for someone to invite him back inside. What makes this even sadder is that his mother relates this fact, earlier, but under the oblivious impression it was a childhood quirk or Trent expressing his artistic sensitivities.
* The outcome of Mr. O'Neill's effort to teach success through failure in "The F Word" was nothing but pure despair for almost everybody, especially for Brittany and Kevin. They may be idiots, but that doesn't mean you can help feeling bad for them.
* There's a small and easy to miss moment in "The Lost Girls." When the Morgendorffers are having dinner with egotistical and deluded magazine editor Val, Daria delivers a small and somewhat scathing explanation on the concept of "Edgy," that is, the idea of marketing executives engineering "This fake concept of seeming to be dangerous" when everything they do is mass produced, planned in advanced, and meant to suck the spending money out of society's younger generation. When Daria finishes speaking, Quinn suddenly looks very depressed, as if she was actually listening to what Daria was saying and understood it. And by understanding it, it's one of those moments when Quinn is forced to face that all the things which make her popular, the clothes she wears, the music she likes, the movies she sees, also make her part of the same bland, faceless crowd that is being willfully exploited for their money. The moment doesn't last long, but it's one of a few times in the first half of the series when Quinn is legitimately saddened by something.
* "Of Human Bonding" has Jake and Daria on a plane en route to a seminar. Earlier in the episode, Helen suggested to Jake that they could bond during that time. Jake thought to himself that maybe he should resolve his DaddyIssues and try to be a better father for Daria, while Daria ponders if she should let her guard down and let her father know that she loves him. Only small talk about peanuts and goldfish escape their lips.