Vanessa, a character in The Freshman series, is a literature student and James's childhood friend. She is first seen in the special book "James: Masquerade Ball".


Vanessa has mid-length, brown hair, blue eyes and light skin. At the masquerade, she wears a blue dress, a silver necklace, a silver mask and silver earrings.


Vanessa is an intelligent young woman.



Vanessa is James's childhood friend. Their parents are very good friends, so James and Vanessa grew up together and they seem very close. At the dinner with James's parents, Mrs Ashton mentions her as the perfect girl for her son.

Vanessa and James haven't seen each other for three years when Your Character and James meet her at the masquerade. She confesses that her father has got some serious problems after making some bad investments and asks James's family for help. Vanessa had (and still has) deep feelings for James. He doesn't see her that way, but he cares about her very much. Vanessa also just wants to see James happy; even if it is with another girl. She is protective of him and calls him one of her dearest friends.

Your Character

You are able to meet Vanessa in James: Masquerade Ball. She will be friendly if you say that you are pleased to meet her. If you introduce yourself as James's date, she will be surprised and emphasize that she and James have a long history. She is okay with you dating James if that makes him happy but tells you not to hurt him, otherwise you would have to answer to her.



  • She is shown on the cover of "James: Masquerade Ball".
  • She makes a cameo appearance in Rules of Engagement, Book 2, Chapter 3.
  • She bears a resemblance to actress Stana Katic.
  • She is majoring in literature with emphasis on early twentieth century writers.
  • Vanessa took ballet together with James. Their parents signed them up.
  • She once wore braces and showed up to dinner with unkempt hair and scrapes from falling off her horse.