Bookish Sister is one of the main characters in the Rules of Engagement series. Her suggested name is "Nicole", but the player can choose a name for her. Her task is to complete the bucket list that was given to her by Nana. She is first seen in Book 1, Chapter 2.


Bookish Sister has brown hair which is tied up in a bun, brown eyes and fair skin. Usually, she wears black glasses and a white sweater over a plaid shirt.


Bookish Sister is an incredibly shy, self-conscious and introverted girl. At first, she only wants to pursue her career in London but gradually becomes more confident and loosens up with the help of Nana's wish list and Audrey.


Rules of Engagement

Book 1

  • Chapter 2: Wine and Mixers
  • Chapter 3: Date with Destiny
  • Chapter 5: Song and Dance
  • Chapter 6: One Day in Athens
  • Chapter 7: Sweet Sixteen
  • Chapter 8: Out of Time
  • Chapter 11: Under Fire
  • Chapter 12: New Heights
  • Chapter 13: On the Spot
  • Chapter 16: Seeing Red
  • Chapter 18: Last Call
  • Chapter 19: The Morning After

Book 2

  • Chapter 2: Dangerous Liaisons
  • Chapter 3: London Calling
  • Chapter 5: Trouble in Paradise (Determinant)
  • Chapter 7: Reality Bites
  • Chapter 10: Royal Pain
  • Chapter 13: Up in the Air
  • Chapter 17: Starry Nights
  • Chapter 18: Moment of Truth
  • Chapter 19: Finale I: Now or Never
  • Chapter 20: Finale II: High Tides
  • Chapter 21: Finale III: Just Say Yes

Book 3

  • Chapter 1: Setting Sail
  • Chapter 2: Piece of Cake
  • Chapter 3: Meet the Family
  • Chapter 4: Painted Sky
  • Chapter 6: Labor of Love
  • Chapter 7: Le Voyage dans la Lune
  • Chapter 8: The Bachelorette
  • Chapter 9: When in Rome
  • Chapter 10: Perfect Fit
  • Chapter 11: Into the Woods
  • Chapter 12: Memory Lane
  • Chapter 14: After the Storm
  • Chapter 15: Everything is Illuminated
  • Chapter 16: Save the Date
  • Chapter 17: After Party
  • Chapter 18: Bon Voyage


  • Chapter 1: Home Sweet Home (Off-Screen)
  • Chapter 2: Autumn Gatherings (Mentioned)
  • Chapter 3: To the Lighthouse
  • Chapter 4: A Harvest Homecoming
  • Chapter 5: Into the Sunset



Main Character and Brother are her older siblings. Party-Girl Sister is her younger twin (but they're very different). One of her favorite memories with Main Character is when they caught fireflies in Nana's backyard. They also used to hang out in a treehouse which kept a telescope. They once snuck out late at night when Bookish Sister wanted to see Neil deGrasse Tyson speaking at a planetarium.


Cousin has always been jealous of Bookish Sister and her siblings because she thinks that Nana loved them more than her. Now, after Nana's death, she tries to get the whole inheritance for herself by sabotaging her cousins' tasks.

Blaire Hall

Blaire was Bookish Sister's idol and she previously wanted to get an internship under her. However, after getting the internship, she realized how cold Blaire was and abandoned her former dream career. They ran into each other in Rules of Engagement: Newlyweds, Chapter 3. She told Blaire that she and Audrey are starting a business together and Blaire is impressed. They parted ways after they talked.


Bookish Sister meets Audrey in a salsa class aboard the cruise. They become dance partners and also very good friends. If the player chooses so, Bookish Sister has a romantic relationship with Audrey. Audrey helps her finish her list and films her while doing so. She invites Audrey to Main Character's wedding in Book 3, where they decide to start a company together.


Bookish Sister meets Paolo when she went to London to get an internship under Blaire Hall. Paolo was another intern and Bookish Sister's competition, as only one could secure a place in Mansingh International. At first he is rude and demanding to her, even trying to get a coffee from her when they first meet, but later apologizes and go to a pub where the player can choose to romantically advance towards him, However, nearing the end of the pub visit, Paolo steals the badge from Bookish Sister to gain an advantage in the internship. In Book 2, Chapter 10, she can either give him a piece of mind or push him into a fountain.

They met again in Rules of Engagement: Newlyweds, Chapter 3, in the airport. Paolo wants to apologize for what he did and invited her to dinner (premium choice). They talked and he asked for her forgiveness for what he did. She can either forgive him or get back at him. They parted ways after their meeting.


It's mentioned by Party-Girl Sister that she used to disguise as her to break up with him.


Other Looks



  • It's revealed in Book 3, Chapter 7, that she's the second youngest granddaughter/grandchild (of Nana), meaning that she's the older twin of Party-Girl Sister.
  • She has a resemblance with Hailee Steinfeld.
  • According to her, the tasks she must complete to obtain her inheritance are the same tasks that her Nana did on her first date with her future husband.
  • The default name Nicole is of Greek origin and means "victory of the people". It's the female French variant of the name Nicholas.
  • If the player decides to have her keep the name Nicole, she subsequently shares the same forename as Nicole Anderson from the Bloodbound series. 
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