|“||I can touch her, Elena. I can kiss her again. And I know it's wrong and I know that I shouldn't feel this way, but I do. I love her. I've always loved her.||”|
Anna was hurt that he wanted this for Vicki Donovan. However, she and Jeremy made up and began a romantic relationship. This, like Jeremy's relationship with Vicki, ended when she was killed.
They are referred to as "Janna" by fans.
While doing his history project, Jeremy Gilbert ran into Anna at the library after she almost knocked books into him. She helped him with his research due to the fact that she was home-schooled and knew the library very well. They came across the animal attacks and Anna suspected that they were vampires as she told him that her grandfather had journals about vampires in Mystic Falls. To prove she was right, she went into a lot of research, but Jeremy was still skeptical. However, at first Anna only wanted his grandfather's journal.
As it turned out, Anna was a vampire who wanted to free her mother from the tomb and needed the Gilbert Journals to find out how to do so. When she asked Jeremy to meet her at Mystic Grill, Damon Salvatore, who also wanted to open the tomb for his lost love Katherine Pierce, convinced Jeremy to go. At the grill, Damon recognized that Anna was also from 1864. At a party, Jeremy saw that Anna's eyes had changed but was knocked out by Ben McKittrick, another vampire. Anna had planned to use Jeremy's blood to feed her mother because it was his ancestor Johnathan Gilbert who was behind her capture, but used his sister, Elena Gilbert, instead.
Once she freed her mother Pearl, Anna told Jeremy that she was leaving Mystic Falls with her, but after Pearl wanted to make her home in Mystic Falls, Anna told Jeremy that plans had changed. By now, Jeremy suspected that there was something else about Anna and started researching vampires himself. When she came around for dinner, Jeremy purposely cut himself with a knife and tempted Anna to drink his blood, although she tried to fight it off, she eventually gave into her own temptations and drank his blood for the first time, thus proving what she really was, a vampire.
She appeared in his room and reprimanded him for what he did, saying she could have killed him and she should have. Jeremy told her he did what he did because he wanted her to turn him. Anna listed the reasons to become a vampire. Jeremy originally wanted to turn because he thought it was the reason Vicki Donovan had left, but when Vicki's body was accidentally discovered by Caroline, Anna realized Vicki was for whom he wanted to change and was heartbroken. After a period of distance, they eventually began a relationship, with her officially enrolling in high school to spend time with him. They both admitted to having used each other in the beginning, but had developed genuine feelings for one another over the course of time they spent together and those feelings led to them sleeping together.
When the tomb vampires planned to attack the Founding Families, which included Jeremy, Anna came to see him. When John Gilbert activated the device, Anna, and all the other vampires in the vicinity were incapacitated. Deputies found them and took Anna away against Jeremy's protests to be destroyed.
Damon Salvatore witnessed her death at John Gilbert's hands before he was rescued by his brother Stefan Salvatore, and told Jeremy. He felt sorry for her and offered to erase Jeremy's memory of her, but Jeremy refused, suggesting that he loved Anna more than he did Vicki. After discussing whether vampire life was better than human life, he drank Anna's blood and swallowed several sleeping pills before falling unconscious.
In The Return, Elena went up to Jeremy's room to find him unconscious. She was relieved when she learned that Jeremy wasn't a vampire. Anna's blood had healed him, but he was disappointed. He then told Elena and Stefan about Anna's death.
In As I Lay Dying, after getting shot and killed by Elizabeth Forbes, Bonnie revived him with the help of Emily (even though she knew there would be consequences). After he was revived, he went back to his home. After hearing strange noises coming from down stairs, he continues to walk down the stairs into the kitchen. He turns around to see his recently deceased ex-girlfriend, Anna. He turns around again to see his other deceased ex-girlfriend, Vicki.
In Disturbing Behavior, Anna is laying beside Jeremy on his bed and calls out to him. This wakes him up and she is joyful that Jeremy can hear her and he states that he was dreaming about her. Later she appears to him while he is with Bonnie, trying to warn him about the darkness. Jeremy then decides to shut her out, which makes her very upset because she doesn't want to be alone.
In The Reckoning, Jeremy asks Anna for information about Mikael. However, she tells him that she doesn't want to help Damon and Katherine, which leads Damon into hurting Jeremy and Anna giving in and telling Jeremy where they can find Mikael.
In Smells Like Teen Spirit, Anna warns Jeremy about darkness she senses around him. She then witnesses the fight between Jeremy and Bonnie and becomes angry at Jeremy because he shouldn't be thinking of her when he's around of or thinking of Bonnie.
Jeremy says that he knows but that he doesn't think that he can stop thinking about her. Anna says that she can't stop thinking about him either and they then discover that they can touch each other to their delight.
In Ghost World, while Anna and Jeremy are in the town square listening to Tobias Fell give a speech and she jokes about how the founders stole from all the vampires. They then hold hands as they watch. When Elena asks Jeremy to try and reach Lexi Branson on the Other Side, Anna tells him that she believes that not all supernatural spirits go there; that some of them find peace. When Elena asks if Anna is there with them, she has Jeremy tell her no because she would not like it. Later, in the Mystic Grill bathroom, Anna and Jeremy share a kiss. Unknown to them, Bonnie has cast an unveiling spell. They are caught by a surprised Elena who yells at them both for their actions.
At the Illumination Night, Anna and Jeremy meet. Jeremy is called by Caroline who accuses Anna of stealing the necklace. Jeremy defends her and says that she would never take it. Elena shows up and also accuses Anna of taking the necklace. Jeremy continues to defend her and tells Elena he loves Anna and he always has. Elena then says he can't love a ghost for the rest of his life. Anna appears with the necklace, Elena then leaves and Jeremy appears shocked that she took it she apologizes for taking it. Anna tells Jeremy that she was scared to be alone on the other side and wanted more time to find her mother. Jeremy tells Anna they can still see each other but Anna response is that they shouldn't thus ending their relationship. Later Jeremy tries to talk to Bonnie, but she tells him to leave before he can explain his actions. Bonnie destroys the necklace (although it comes back) and the ghosts disappear. However just before the spell Anna is reunited her mother and at the end of the episode and they both vanish, finding peace.
- Anna: Oh my god. I am so sorry. There was this one book wedged between the other. And I pulled and then kaplunk, kaboom. Are you ok?
- Jeremy: Yeah, I'm fine.
- Anna: Ohh! I'm Anna.
- Jeremy: I'm Jeremy.
- -- Bloodlines
- Anna: Maybe we can have a fright night and rent a whole bunch of vampire movies.
- Jeremy: Uh..Yeah, yea sure.
- Anna: Why does that sound like a no way in hell?
- -- Bloodlines
- Anna: Hey, um... do, do you wanna do something later, maybe?
- Jeremy: Oh, sorry, I'm stuck on punch duty at the school dance.
- Anna: Oh. How'd you get stuck with that?
- Jeremy: Well, I'm failing English, so I copped a plea.
- -- Unpleasantville
- Anna: You just couldn't live without me, huh?
- Jeremy: Well, I kinda miss my daily dose of cute stalker chick.
- -- Children of the Damned
- Anna: "So you're finally ready to go out with me, are you?"
- Jeremy: "It's been a while since I've been to a party, and I kinda wanna get back out there. You know, not be such a loner. And, uh, I like you. You're fun, and...you're also kinda strange and lurky, but, uh, I guess I like that too."
- -- Fool Me Once
- Jeremy: Why didn't you... kill me?
- Anna: I don't know. Maybe I'm a sucker for guys like you.
- Jeremy: Like what?
- Anna: Lost. But why would you confront me about it? Why would you risk it?
- Jeremy: Because if it was true, maybe... I don't know. Maybe it's true about Vicki. And also because... I want you to turn me.
- -- There Goes the Neighborhood
- Jeremy: Come on, you can't keep saying no to me.
- Anna: Look, I'm not gonna turn someone who learned everything he knows about vampires from Netflix.
- -- Let The Right One In
- Jeremy: There's a part of me that's so angry.. that she covered up what happened to Vicki and erased my memories, but.. there's also this other part of me that's glad. I..I don't want to remember Vicki like that.
- Anna: As a monster?
- Jeremy: No, as someone who wanted to hurt me.
- Anna: When I met you, you were just a part of my plan to get my mother back, but then things changed. All the time we spent together. I would never do anything to hurt you..not now..you know that right?
- Jeremy: Yeah, I know that.
- -- Miss Mystic Falls
- Anna: Your uncle John wants us dead.
- Jeremy: Oh, you don't know that.
- Anna: Yes, I do. He's a hater, Jeremy.
- Jeremy: Well, I'm not.
- Anna: No. You're something else entirely.
- Jeremy: Oh, yeah? What would that be?
- Anna: My weakness.
- -- Blood Brothers
- Jeremy: You’re leaving?
- Anna: I’ve been thinking, you can come with me, I could turn you. I mean, you said you wanted me to.
- -- Founder's Day
- Anna: Jeremy, tell me you can hear me!
- Jeremy: Yeah, yeah, I can hear you, all right! What the hell? What is it?
- Anna: I've been trying to get you to hear me for days. Yelling your name, screaming.
- Jeremy: You have?
- Anna: (nods) What changed? I've been trying to get through to you. Why now?
- Jeremy: I was dreaming about you. I...
- Anna: (smiles) You were dreaming about me?
- Jeremy: I can't believe this is actually happening; that you're actually here.
- Anna: I'm here.
- -- Disturbing Behavior
- Anna: It's a two-way street, Jeremy. I only pop up when you're thinking about me. That's why you haven't told her. Isn't it? You don't want her to know you still care.
- Jeremy: I can't do this right now. I can't. This is just too much.
- Anna: I'm sorry. I shouldn't have said that.
- Jeremy: Good-bye, Anna
- Anna: Don't! Jeremy, please. Don't shut me out.
- -- Disturbing Behavior
- Anna: I'm not helping them.
- Jeremy: No, it's ok to help, They're looking for a way to stop Klaus.
- Anna: I don't care. Katherine is not a friend to you. Neither of them are.
- -- The Reckoning
- Anna: Why are you thinking about me when you're calling her?
- Jeremy: I didn't think I was! [...] I don't think I can stop thinking about you.
- Anna: I can't stop thinking about you either.
- -- Smells Like Teen Spirit
- Anna: I need you to believe me.
- Jeremy: I shouldn't even be talking to you. This is not ok.
- Anna: Then send me away. I'm only here, because you want to be with me as much as I want to be with you. Send me away, Jeremy. It's that easy.
- Jeremy: I don't know why this is happening. Or when it's going to stop. But before it's done, I have to do this.
- -- Ghost World
- Jeremy: This.. This doesn’t have to be goodbye.
- Anna: No.. but it should be. Elena was right. I'm holding you back.
- -- Ghost World
- Jeremy discovered what Anna was after gradual suspicion and research in a similar manner to how Elena discovered what Stefan was.
- Jeremy and Anna actually fell in love twice; when Anna was a vampire and after she became a ghost.
- Anna was murdered by John Gilbert, but Jeremy never hated him for it.