Trip is friendly towards the player during the beginning of the game, and is relatively tolerant to the player's actions; for example, if the player says obscenities, he may attempt to laugh it off by saying "you're never afraid to push our buttons" or "you are not afraid to test my patience". Despite this, he is somewhat irritable, and can force the player to leave if provoked enough. It is implied by Grace that he is a very controlling and even manipulative person as she states that he manipulated her into marrying him. This is implied in his recounting of his proposal to Grace, in which he proposed to her in front of her parents on Christmas Eve. It is also stated in a couple of endings how he manipulated Grace into going into something besides art, as she dreamed.

Grace was born in a rich family. When she was growing up, she was spoiled and given everything she had wanted. Grace went to the same college as Trip and the player. In their senior year of college, the player got Trip and Grace to meet each other and start dating. Trip proposed to her on Christmas Eve in front of her parents that year; she accepted the proposal and later married him. She was interested in pursuing an art career, but was convinced by Trip to go into advertising after college, which she let happen due to being unsure about her success. Despite this, she continued to have interest in becoming an artist, and began painting in secret.