The Ruby Oliver Quartet is a series of young adult novels by E. Lockhart. It follows the high school career of Ruby Oliver, a neurotic, hyperverbal girl who starts seeing a shrink after being backstabbed by her best friend. Over the course of the series, she attempts to sort out her various issues with school, friends, family, and boys, all while trying to retain her sanity.

!!! Books in the series:
* ''The Boyfriend List: 15 Guys, 11 Shrink Appointments, 4 Ceramic Frogs, and Me, Ruby Oliver''
* ''The Boy Book: A Study of Habits and Behaviors, Plus Techniques for Taming Them''
* ''The Treasure Map of Boys: Noel, Jackson, Finn, Hutch, and Gideon--and Me, Ruby Oliver''
* ''Real Live Boyfriends: Yes. Boyfriends, Plural. If My Life Weren't Complicated, I Wouldn't Be Ruby Oliver''

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!!This series provides examples of:
* 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.
* BeCarefulWhatYouWishFor: During ''The Treasure Map of Boys'', Ruby wishes that the bad feelings between her and Jackson would go away. [[spoiler: Jackson proceeds to flirt with her at every opportunity, which messes up her truce with Kim and later causes Noel to shun her.]]
**Also "Just once, I'd like to see a situation with too many ''guys.''"
* BecauseISaidSo: Ruby’s mother, quite frequently.
* BitchInSheepsClothing: Kim.
* BittersweetEnding: ''The Boyfriend List'' ends [[spoiler: with Ruby still ostracized but slowly working towards regaining her life and gaining friendships with Meghan, Noel, Hutch and Nora]].
** ''The Treasure Map of Boys'' ends with [[spoiler: Ruby losing Nora’s friendship and ruining her reputation at school again; however, she and Noel finally begin a relationship.]]
* BrandX: Averted for the most part. While Tate Prep itself is fictional and the author occasionally takes creative liberties with certain locations in order to serve the story, she uses real places in Seattle for the story (such as the B&O).
* 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.]]
* BroodingBoyGentleGirl: Noel and Ruby.
* ClassTrip: The latter half of ''The Boy Book'' takes place during November Week, a yearly event in which students go on various outdoor trips—like kayaking and mountain-climbing—for the week. Oddly, November Week isn’t mentioned at all in ''Real Live Boyfriends'', despite the month of November coming and going during the book.
* CrazyJealousGuy: [[spoiler: Noel]] gets this way if he thinks Ruby likes another guy.
* DatingDoSiDo: Pretty much everyone at Tate, but especially Ruby.
* 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.
** Angelo is non-existent after ''The Boy Book''.
* DisappearedDad: Meghan’s dad died when she was young; Noel’s parents are divorced.
* DitzyGenius: Although Meghan is an intelligent student, she never really seems to realize that almost every girl in school hates her.
* DoggedNiceGuy: Various guys, like Finn to Kim and Angelo and Gideon to Ruby.
* DramaQueen: Ruby's mother.
* DudeMagnet: Ruby and Meghan. Both of them are a bit oblivious about it.
* EatingLunchAlone: Ruby, especially in ''The Boyfriend List''. This improves as time goes on.
* FemaleGaze
* FootnoteFever
* ForbiddenFruit: By the time Ruby realizes her feelings for Noel, [[spoiler: Nora, who happens to be one of Ruby’s only friends, has already declared that she likes Noel, and Ruby is now unable to act on her feelings without risking her friendship with Nora.]]
* FormerFriendOfAlphaBitch: Ruby [[spoiler: and later, Nora,]] to Kim and Cricket.
* FriendlessBackground. Hutch, who is a 'social leper' at Tate.
* FriendsWithBenefits: Ruby and [[spoiler: Angelo]] hook up a few times in ''The Boy Book'', but it trails off relatively quickly.
* GreenEyedMonster: Ruby with Jackson and, later, Noel.
* HeroicBSOD: [[spoiler: While Noel is visiting his brother in New York City, his brother's boyfriend dies in an accident right in front of him. He proceeds to push Ruby away and attempt to ignore his feelings about the matter.]]
* HiddenDepths: Ruby initially judges Meghan pretty harshly, but eventually sees what a kindhearted and loyal person Meghan really is, and by the second book the two have become friends.
* InvisibleParents: Aside from Ruby’s mother and father, most of the parents in the series are either rarely mentioned or just never seen.
* KarmaHoudini: Kim gets away with destroying Ruby’s reputation, although [[spoiler: she does end up getting dumped by Jackson in ''The Treasure Map of Boys''.]]
* LoveTriangle: Ruby ends up in more than one.
** LoveDodecahedron: Meghan/Finn/Kim/Jackson/Ruby/Noel/Nora. And that's without even mentioning things like Ariel and Noel hooking up, Jackson cheating or Ruby's various boyfriends.
* LustObject: Ruby has a couple of these, mostly Gideon and Angelo.
* MarsAndVenusGenderContrast: Part of the point of the entire series.
* MatchmakerCrush: Ruby attempts to give [[spoiler: Nora]] advice about her feelings for Noel, despite having recently realized her own feelings for him.
* {{Meganekko}}: Ruby
* MistakenForCheating: [[spoiler: Noel]] thinks this about [[spoiler: Ruby]] twice, once in ''The Treasure Map of Boys'' with [[spoiler: Jackson]] and once in ''Real Live Boyfriends'' with [[spoiler: Gideon]]. It does not end well either time.
* NotGoodWithPeople: Hutch, who is even more of a social outcast than Ruby. He does eventually befriend Ruby and Noel.
* OhCrap: Ruby gets a pretty big one in ''The Treasure Map of Boys'' when [[spoiler: Ariel catches her and Noel kissing.]]
* 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, but it never goes anywhere.
* SavvyGuyEnergeticGirl: Ruby's parents.
* SecondLove: [[spoiler: Noel for Ruby, Finn for Meghan.]]
* SelectiveObliviousness: Ruby is implied to have suffered this in regards to Jackson and Kim.
* SexWithTheEx: Ruby with Jackson, though only as far as kissing.
* ScholarshipStudent: Ruby and Finn.
* ShipperOnDeck: Nora does a little of this for Ruby and Gideon, and Meghan for Ruby and Noel.
* SlutShaming: Ruby is on the receiving end of this trope. Her Boyfriend List is MistakenForEvidence of her slutty ways, and Ruby's ex friends write graffiti about it in the girls' bathroom at Tate.
* StalkerWithACrush: [[spoiler: Ariel]] acts this way during ''The Treasure Map of Boys'' after [[spoiler: she and Noel hook up.]]
* TemporaryLoveInterest: During ''The Boy Book'', Ruby hooks up with [[spoiler: Angelo]] a few times. In ''Real Live Boyfriends'', while [[spoiler: she and Noel are broken up, she briefly dates Gideon.]] Of course neither of these last more than a few chapters.
* ThereAreNoTherapists: Averted with Ruby and Meghan, both of whom are in therapy for the duration of the series.
* WardrobeMalfunction: A chemistry class incident in ''The Treasure Map of Boys'' ends with Ruby in a wet white T-shirt and an orange bra very visible underneath.
* 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; it's never confirmed either way, but Ruby views it as a probability.