History VisualNovel / RulesOfEngagement

Katie must be married at the end of the cruise, Jess has to keep a job as part of the staff, Nicole must become more adventurous, and their brother Alex must take his assistant Elena out on dates.

** Jess is in a TriangRelations with both Carter and Blake. Alternatively, she can also date Mira.

** Book 2 Chapter 11 has Cassandra and Ana from VisualNovel/MostWanted sitting at the blackjack table at the casino in Cordonia. At the roulette table is Ryan and Alyssa.

* EvilAunt: Aunt Mallory is this to Katie and her siblings.
* EvilMatriarch: Aunt Mallory is making sure her nephew and nieces don't get their share of the inheritance, by making Violet trip them or breaking their drives herself.

* WhamEpisode=/=SequelHook:

* WhamEpisode: From the book finales, which also serve as [[SequelHook Sequel Hooks]].

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* MilitaryBrat: Book 2 Chapter 4 has Dean reveal he is one, and he later joined the UsefulNotes/NavySeals.

* UsefulNotes/NavySeals: Book 2 Chapter 4 has Dean reveal he used to be one of them.

* WhamEpisode: Book 1 Chapter 19 has quite a lot of it. [[spoiler: Jess wakes up in bed with her boss and only a premium choice allows her to recall what happened. Nicole leaves the ship to pursue her career. Regardless of who Katie chose between William, Leo or even Dean, Trent drops a bomb that the paperwork that you signed that was in Greek...is a marriage license, meaning she's now married to a lying, cheating scumbag!]]

** Blaire Hall is a more downplayed version. She isn't outright cruel to her daughter Grace, but she behaves rather coldly toward her, clearly valuing her work a lot more than her daughter.

* YourCheatingHeart: Katie walks in on her ex-fiance Trent with another girl. She lets him clearly know the two of them are done.

* BiTheWay: Nicole can be this if the player chooses to hook her up with Audrey and Paolo.

* GoodBadGirl: Jess. She is a Party Girl who has very casual relationships and one-night stands, but also a caring and loyal sister.

** Book 2 Chapter 21 is no slouch either. [[spoiler: Katie gets engaged to one of her suitors, but before you can truly enjoy it Aunt Mallory comes and announces that she looked carefully at the will and the ExactWords refers to Elena as his girlfriend of two years, of which there is no evidence of on social media, meaning unless they find evidence they have been dating for two years he’s out of his inheritance. Meanwhile Mallory had Violet interrogate Mira and later Tina the waitress, who mentioned seeing Jess and Blake together after hours. While there’s no evidence, even a hint of something untoward means one of them has to go, so Jess quits and has to find a new job or she’s out of her inheritance. As if having two of the siblings having their inheritance in doubt, Dinesh reveals they and their cousins have a second set of tasks set out by their Nana to complete to earn their inheritance!]]

* WhamEpisode: Book 1 Chapter 19 has quite a lot of it. [[spoiler: Jess wakes up in bed with her boss and only a premium choice allows her to recall what happened. Nicole leaves the ship to pursue her career. Regardless of who Kate chose between William, Leo or even Dean, Trent drops a bomb that the paperwork that you signed that was in Greek...is a marriage license, meaning she's now married to a lying, cheating scumbag!]]

** In the final chapter of Newlyweds, Mallory reveals why she felt her was favored, [[spoiler: She was dating a man who her parents hated, she felt this was unfair because they always loved whoever her sister dated. In a fit of anger she destroyed a dollhouse she and Nana built together. It turned out her parents were right, her boyfriend was emotionally abusive and didn’t want a kid when she was revealed to be pregnant with Violet. In the end it turns out Nana had left her the lake house and a small fortune of her own and had rebuilt the dollhouse]].

** In book 3 it’s slowly revealed [[spoiler: This is not true at all, in fact Violet used to be extremely close to the siblings, until her mother got in the way. Mallory was the one who truly felt her mother favored her sister over her. It was after the siblings’ parents died and Nana fought to gain custody of them over Mallory despite not being in the best of health even then, that convinced her her mother didn’t trust her. Nana had no choice but to accept when Mallory separated Violet from the siblings. Violet’s inheritance is revealed to be she has to get the siblings to agree that she can have her inheritance, this to prove to her she is loved.]]

* EccentricMentor: Blair’s Hall can be quite... odd at times.