Of all the characters on The Vampire Diaries who wound up on the Other Side, Elena and Jeremy Gilbert's aunt, Jenna Sommers (Sara Canning), wasn't one of them. The Vampire Diaries was created by Julie Plec and Kevin Williamson and ran for eight seasons on the CW. The series' success can be attributed to its attractive ensemble cast and its ability to put a unique twist on the typical coming-of-age story by intertwining it with bone-chilling horror and supernatural fiction involving witches, vampires, and werewolves.
During The Vampire Diaries' first two seasons, Miranda Gilbert's sister Jenna served as Elena and Jeremy's legal guardian. Season 2's main story arc involved Klaus Mikaelson's plan to break the Hybrid Curse placed on him 1,000 years earlier by his mother, Original witch Esther Mikaelson. The key ingredients to break the curse involved sacrificing a doppelganger (Elena), a vampire (Caroline Forbes), and a werewolf (Tyler Lockwood). In a last-ditch effort to thwart Klaus' plan, Damon rescued Caroline and Tyler, failing to realize that Klaus had already chosen backups. Once the ritual began, Elena discovered Klaus had turned Jenna into a vampire (with some help from Katherine Pierce, who, like Elena, was a Petrova doppelganger). In one of the series' most heartbreaking moments, Elena stood by helplessly and was forced to watch Klaus murder Jenna during season 2's penultimate episode, "As I Lay Dying". Surprisingly, despite this and other numerous acts of heartless brutality, Klaus became such a popular character that he received his own spinoff, The Originals.
The Vampire Diaries' creators made bold choices when it came to killing off beloved characters (arguably the most shocking was Stefan Salvatore, who died in the series finale), but many were able to return due to the existence of the Other Side, a purgatory for supernatural characters created by the powerful witch Qetsiyah. Throughout five seasons, the Other Side offered a loophole that enabled fan-favorites to rejoin the series for the short- or long-term, but Jenna remained conspicuously absent. Esther, who spent 1,000 years on the Other Side as punishment for turning her children into vampires, confirmed Jenna's fate during season 3, episode 20, "Do Not Go Gentle". Esther assured Elena that Jenna was not on the Other Side. "You may draw comfort knowing that your aunt is not in the place I was. She doesn't know the torment of the Other Side. Though made a vampire, she remained pure, and she knows peace...which is all any of us can hope for."
In a 2011 interview with TV Guide, Plec revealed that Jenna's death hadn't been planned until they began writing episode 20. When questioned about the potential blowback from fans, Plec stated:
"With series regulars you're always going to have fan-bases that feel very protective of them and love them and feel like they're family so these decisions are not going to go over necessarily well all the time. But we spent an entire season building to this sacrifice ritual and bringing Klaus in and we felt like the loss of life in the sacrifice ritual needed to be as deeply personal as possible in order to show how big of a move it was that Klaus is making and how profound of an impact it would have on not only Elena's life, but on everybody."
Sara Canning briefly reprised her role as Jenna during The Vampire Diaries season 5, episode 11, "500 Years of Solitude". Everyone gathered together to celebrate the final moments of Katherine's life, who was dying of old age (a dangerous side effect of the Cure). Jenna appeared not as herself but as a hallucination Damon planted in Katherine's head. During the final moments of the series finale, Elena's death allowed her to reunite with most of her family, including her adopted parents Miranda and Grayson, her biological father John Gilbert, and Jenna.