History Literature / RubyOliverQuartet

* BreakUpToMakeUp: Ruby pines for Jackson in some way, shape, or form throughout the first three books. With the help of her friends and therapist (not to mention her increasing feelings for Noel), she eventually comes to terms with the fact that Jackson was and always will be a jerk, [[spoiler: and when he asks her out again at the end of ''The Treasure Map of Boys'', she shoots him down cold.]]

* AdultsAreUseless: Zigzagged with Ruby's parents.
* AlmightyMom: Ruby’s mother.
* AlphaBitch / GirlPosse: Heidi, Katarina, and Ariel make up a girl posse of alpha bitches. [[spoiler: Kim and Cricket are eventually added.]]
* AnnoyingYoungerSibling: Jackson’s younger sister Dempsey.

* CrazyJealousGuy: [[spoiler: Noel]] gets this way if he thinks Ruby likes another guy.

* DemotedToExtra / PutOnABus: By the fourth book, a number of characters have disappeared from the series, mostly because it's primarily focused on Ruby and Noel's relationship. Kim and Cricket are hardly mentioned; Jackson has graduated and is now attending Cornell; Hutch spends the semester in Paris.

* DramaQueen: Ruby's mother.

* FootnoteFever

* NotGoodWithPeople: Hutch, who is even more of a social outcast than Ruby. He does eventually befriend Ruby and Noel.

** Angelo is non-existent after ''The Boy Book''.

* FatalFlaw: Ruby herself notes she has a bad habit of sticking her nose in other people's business, even when it would be really sensible not to do so.

* {{Meganekko}}: Ruby, which is one of the only visual clues we have about what she looks like.

* DitzyGenius: Although Meghan is an intelligent student, she never really seems to realize that almost every girl in school hates her.
** Subverted in ''Real Live Boyfriends''; as part of her interview for Ruby's film, Meghan discusses her previous views of popularity and her eventual realization that Ruby and Nora were the first real friends she ever had.

* ParentalObliviousness: Downplayed with Ruby’s parents; neither of her parents ever seem to notice the true amount of crap that their daughter has to deal with, but Ruby's mother does bring up that Ruby has stopped hanging out with Kim and Cricket.
* PrecociousCrush: Ruby has a vague one on one of her teachers, Mr. Wallace, but it never goes anywhere, for obvious reasons.

* WithFriendsLikeThese: Kim and Cricket are horrible friends to Ruby and Nora. Ruby herself can also be a pretty bad friend, although it's not at all out of malice and more because she has a tendency to get involved in things she shouldn't out of a desire to help others. Nora in the latter half of ''The Treasure Map of Boys'' treats Ruby pretty badly.
* YourCheatingHeart: This seems to be a chronic problem with Jackson. He cheats on Kim while she's on an exchange program in Tokyo, and it's implied that he cheated on Ruby with Kim; they both obviously deny it, but Ruby eventually admits to herself that he probably did cheat.

* {{Meganekko}}: Ruby

* WhateverHapppenedToTheMouse: In-universe, Ruby complains about a guy called Billy, who kissed her and asked for her number, then never called her, wondering why you'd go to the trouble of asking for a number and then not calling it.