James Ashton

James, a main character in The Freshman, The Sophomore and The Junior series, was an upperclassman at Hartfeld and is one of your love interests. He graduated in The Sophomore, Book 1, Chapter 15. He is first seen in The Freshman, Book 1, Chapter 1.

Appearance
James has cropped, black hair, brown eyes and dark skin. Before his redesign, his facial feature was different and his skin tone was lighter. His left eyebrow is raised. Usually, he wears a blue blazer and a gray shirt.

In The Sophomore, he wears a blue jacket over a gray shirt.

Personality
James acts very professional. Even though he likes being sarcastic, he's very respectful to other people. Writing is James' passion, he's incredibly dedicated to becoming an author and playwright.

Words mean everything to him. James tells Your Character that he will only say "I love you" to the girl intends to stay with for the rest of his life. James thinks of himself as composed, confident and cool, but at times has shown to be unsure of himself and hesitant in important decisions. He's also very popular with the girls because of his name, his money and his appearance. It's unclear if James is aware of these reasons, but if he is, he doesn't seem to care about it very much. James seems very unapproachable at the beginning. After he reveals to his parents that he is studying literature, he begins to open up more. He can be very hurt by the people he cares about the most.

The late Professor Vasquez appears to have a profound lasting effect on James, as is shown in Book 3, Chapter 11, when, while Your Character is talking about the group's problems to him over Skype, James has muted his mic and is writing up details to a story he is writing using inspiration from Your Character, much like Vasquez did with his daughter Gabriela and Your Character.

His parents
James has a somewhat complex relationship with his parents George and Olivia Ashton. They want him to take over their investment company and to marry a prosperous girl. Not wanting to disappoint them, he originally delayed telling his parents he's studying literature and wants to be a writer. To stop their matchmaking actions, he introduces Your Character to his parents as his fiancee.

Enrique Vasquez
"Your classes ignited a passion in me. You taught me the power and beauty of the written word, something I hope to dedicate my life to. Thank you, Professor Vasquez. For everything. - James at Vasquez's grave in Book 3, Chapter 9"

Vasquez is James's mentor. He helps James to write the play "Rosethorne Park", while James helps Vasquez with technical problems and other things. At the beginning of the story, they have been working together for three years. Vasquez means very much to James. He's the only one who understands James' passion for writing and supports him. Vasquez has got James' respect and trust. As James finds out about Vasquez's cancer, he feels hurt and unsure of how to behave near his mentor. These feelings of conflict are resolved after Vasquez reconciles with his daughter, Gabriela, and witnesses the birth of his grandson, Enrique Vasquez II.

Your Character
As soon as she starts working for professor Vasquez, Your Character and James become Co-Workers. At the beginning, he appears to dislike her as suggested by his teasing. After they spend more time with each other at the Kappa Phi Sigma ball and the dinner with his parents, James softens up. He even defends Your Character from Professor Vasquez because he cares about her and doesn't want her to leave Hartfeld.

In The Sophomore, Book 2, if you help raised James's confidence, he will give you an early copy of his new book as a token of appreciation.

Vanessa Kingsley
Vanessa is James's childhood-friend. Their parents are very good friends, so James and Vanessa grew up together and seem very close. At the dinner with James' parents, Mrs. Ashton mentions her as the perfect girl for her son. Your Character is able to meet her at the masquerade ball with James. She confesses that her father has got some serious business problems and asks James' family for help. Vanessa had (and still has) deeper 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's with another girl.

Sebastian
"He's just from a different world, you know - James about Sebastian in Book 2, Chapter 2"

James and Sebastian know each other from prep school. He describes the sophomore as a talented actor and a textbook narcissist. They seemed to be friends and James respects Sebastian very much for his abilities but he is disappointed in how Sebastian treats those students of lower class than himself, mentioning that he was different back in prep school. After this, James turns his back on Sebastian and supports his rival Chris at the campaign. He then apologized to James for his behavior.

Reyna Mercado
Reyna is a potential love interest for James (if he's single). In The Sophomore, Book 1, Chapter 15, he chose Reyna to be the new editor-in-chief for next quarter. Same system as the confidence, In The Sophomore, Book 2, if James's is single and if you encourage his interest to Reyna, they become official in Chapter 13 or remain as friends.

Trivia

 * He is shown on the cover of The Freshman, Book 4, James: Masquerade Ball, The Freshman: Game of Love, The Freshman: Snowed In, The Sophomore: Hartfeld Horror Story, and The Junior, Book 1.
 * In James: Masquerade Ball, it is revealed that as a child James had a stuffed bunny named Tabitha.
 * It is also found out that James took ballet lessons alongside Vanessa.
 * In Snowed In, he mentions that he is looking forward to celebrating Kwanzaa, although his family celebrates Christmas as well.
 * He is from New York.
 * Prior to his redesign, he used to resemble actor Michael B. Jordan. However Pixelberry updated his face on October 17th, 2017.
 * His new portrait features darker skin and different facial features. His wardrobe and beard shape remain the same. Pixelberry explained in a blog post that this change, like any that might be made to established characters, was made to make it clear that all characters in their stories are fictional and not based on specific individuals.
 * They also stated that while other characters appearances may change, they will not alter the appearance of other love interests.
 * Whilst your character is a freshman (first year), James is a senior, possibly a "fifth year" or "super senior" when your character becomes a sophomore (second year).
 * He took an extra semester due to missing a quarter in The Freshman, Book 3 when he left for LA to make a movie version of his play.
 * He graduated from Hartfeld in The Sophomore, Book 1 which happened in Chapter 15
 * In Helen Twombly's story in The Sophomore: Hartfeld Horror Story, he is renamed Jim and is portrayed as a much more stereotypical nerd.
 * If Your Character has been dating James since the beginning of The Freshman Series, in Book 2 Chapter 4 of The Sophomore, the two of you celebrate your one year anniversary.
 * In The Sophomore, Book 2, if you helped raise James's confidence, he will give you an early draft of his new book as a token of appreciation in Chapter 13.
 * In  Chapter 15 of The Sophomore, Book 2,  if you are dating him, he will ask you if you if want to move in together.
 * If he is also your love interest, he will be the one to get in the car with Tyler and Abbie.
 * In The Junior, Book 1, Chapter 1, if you are dating him, he will move out of his apartment and into your new one.
 * In The Junior, Book 1, Chapter 2, you have the chance to give him a makeover.