Jessica "Jess" Moore

Jessica "Jess" Moore was the girlfriend of Sam Winchester and commonly considered to be the love of his life considering that he has not had any serious relationships since her, or even hook-ups like his brother, Dean, commonly does. They met at Stanford though the exact timing is unknown. She and Sam were serious enough that Sam was considering proposing to her, he planned on shopping for engagement rings sometime before he got back into hunting. However, right before a big test at school for him and right after a Halloween party, his brother, Dean, shows up, claiming that their father, John is in danger and that Sam needs to come help him. Jessica urges him to stay, reminding him of the law school interview he has coming up. He tells her he'll make the interview and tells her not to worry. Sam kept his secret life hidden from Jessica, she had no clue that her boyfriend was from a family of hunters that hunted the supernatural and that the real reason John was missing was because he had gone missing on a hunt.

Right before Sam is due to come back to Stanford, Jessica is attacked by Brady, a friend of theirs who was possessed by Azazel. Jessica dies in much the same way as Sam's mother, Mary died, twenty-two years previously. Sam is grief-stricken by her death and this is the sole reason he goes back into the hunting life. Throughout much of the first and second season, he is shown to be afraid to move on, he misses her and still grieves her.

In the alternate reality that the Djinn created, Jessica was alive and she and Sam were engaged, living in Windom and very close with Adam and Dean and Adam's mom and dad.