|“||Well, I bet it was the men who made a big deal about being founders back in 1860. Men are very territorial.||”|
Elijah and Jenna became friends after the former approached the latter seeking information about the history of Mystic Falls; however, though Elijah seemed to like Jenna, his intention in befriending her was not only to gain information, but to also get closer to Jenna's niece, the doppelgänger Elena Gilbert. During the time they knew each other, Jenna and Elijah had a slightly flirtatious relationship, as seen during their interactions in The Dinner Party.
Throughout The Vampire Diaries Series
In By the Light of the Moon, Jenna told Alaric that she had plans to help a writer who was doing some research on small towns in Virginia because Carol was unable to do so herself; since Jenna's sister Miranda Sommers had most of the archives boxed up at the Gilbert house, it made the task easier for Jenna. When Elena returned home, Jenna asked her to help her with the box, just as Elijah appeared from around the corner and said, "Hi, I'm Elijah," despite knowing that Elena already knew who he was. Jenna, upon seeing Elena's surprise, explained to her that Elijah was the writer she had been talking about, and she and Elijah made plans to have the boxes picked up for him. Before he left, he thanked Jenna for inviting him into the home and told them that he hoped to see them soon.
In The Dinner Party, Elijah and Jenna discussed the history of Mystic Falls at the Mystic Grill. During their discussion, Elijah informed them that the Founding Families didn't actually found the town at all, and that in reality, the witches who had migrated from Salem had lived there long before the so-called founders. Shortly afterward, Alaric, the history teacher and Jenna's boyfriend, joined them at the table and their discussion of the town's history. When they run into Damon and Andie, the latter invited both Jenna and Elijah to a dinner party at the Salvatore Boarding House that evening, and they both accepted. However, when Elijah arrived that night, he warned Damon not to cross him before leaving to greet Jenna and compliment her on how "incredible" she looked. Jenna thanked him for the compliment just as they all sat down for their meal. Elijah went into further detail about the Salem witches in Mystic Falls, and how a majority of them were believed to be burned to death somewhere in town.
In order to get Elijah alone, Damon compelled Andie to convince Jenna to help her with dinner, allowing him to have a drink with Elijah while they were waiting. Before the ladies had finished their dinner, Alaric stabbed Elijah in the heart with a white oak ash dagger, and Jenna was given a fake excuse to leave the party early.
In The Last Day, when Alaric arrived at the boarding house, Jenna aimed a crossbow at him, believing him to still be possessed by Elijah's brother Niklaus. Before she could hurt him, however, Elijah and Elijah ran downstairs to stop her. Later, when Alaric explained the story of what he could remember happening to him, both Jenna and Elijah were there to listen as well.
In The Sun Also Rises, Elijah, Stefan and Alaric were preparing for the sacrifice during the time that Jenna was kidnapped by Klaus and turned into a vampire so she could serve as one of the three sacrifices to break his hybrid curse. After they learned that Klaus was planning to sacrifice Jenna, they all began to plan to help save her, and Elijah supported Stefan's attempt to convince Klaus to sacrifice him instead. Unfortunately, Klaus rejected Stefan's offer and killed Jenna anyway, with her friendship with Elijah ending along with her life.
- Jenna: "So you're welcome to stay here and rummage through this stuff or Elena and I could help you load it into your car."
- Elijah: "Or I can get someone to pick it up tomorrow."
- Jenna: "Also a good plan."
- Jenna: "The old Fell property actually starts just beyond that fence."
- Elijah: "Ah, the Fells. One of the Founding Families."
- Jenna: "Why do you say it like that?"
- Elijah: "My research showed me that this area was actually settled almost two full centuries earlier. It was a migration of townsfolk from the northeast, um, it was Salem, to be precise."
- Jenna: "Massachusetts? As in the witch trials?"
- Elijah: "Which means the ever-lauded founding families...didn't actually found anything."
- Jenna: "Well, I bet it was the men who made a big deal about being founders back in 1860. Men are very territorial."
- Elijah: "Jenna. Wonderful to see you again. How are you??"
- Jenna: "Nice to see you."
- Elijah: "You look incredible."
- Jenna: "Thank you."
- Alaric was a little jealous of their relationship, a fact that Damon was aware of and often used to tease him.